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Extracurricular laboratory: Synthetic route of 81900-93-8

81900-93-8, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,81900-93-8 ,4-Aminobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Name is 4-Aminobenzo[d]oxazol-2(3H)-one, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 81900-93-8, its synthesis route is as follows.

Amine 2b (289 mg, 1.2 mmol) (Scheme 7) was dissolved in 20ml of AcOEt and at 0C triphosgene (356 mg, 1.2 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound lb (180 mg, 1.2 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave lOOmg of a white solid. Yield = 20% ‘HNMR (DMSO, 200 MHz) delta 1.94 (4H, m), 3.23 (4H, m), 4.67 (2H, d, J = 5.6 Hz), 6.55 (2H, dd, J = 8.8 Hz, J’ = 1.2 Hz), 7.05 (1H, t, J = 8.2 Hz), 7.17 (2H, d, J = 7.2 Hz), 7.46 (1H, d), 9.98 (1H, t), 1 1.53 (1H, bs), 1 1.80 (1H, bs); [M+1] 421.2 (C2oH19F3N4O3 requires 420.39).

Reference：
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

The important role of 81900-93-8

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4-Aminobenzo[d]oxazol-2(3H)-one, 81900-93-8

81900-93-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4-Aminobenzo[d]oxazol-2(3H)-one, cas is 81900-93-8,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Example 33: 1-(4-chlorobenzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea (scheme 1) Preparation of 1-(4-chlorobenzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Commercially available p-chlorobenzylamine (1.6 g, 11.4 mmol) was dissolved in 60ml of AcOEt and at 0C triphosgene (3.38 g, 1equiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 30 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1b (1.7 g, 11.4 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 7 / petroleum ether 3). The solvent was evaporated and the crude was dissolved in AcOEt (80 ml) and washed with water (1 X 50 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 500mg of a white solid. Yield = 14% 1HNMR (DMSO, 200 MHz) delta 4.57 (2H, d, J = 5.8 Hz), 6.53 (2H, m), 7.04 (1H, m), 7.41 (4H, s), 9.88 (1H, t), 11.53 (1H, s), 11.80 (1H, bs); [M+1] 318.5 (C15H12ClN3O3 requires 317.73).

Reference：
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Downstream synthetic route of 4-Aminobenzo[d]oxazol-2(3H)-one

Example 32: 1-(4-(trifluoromethyl)-2-morpholinobenzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea (scheme 1) Preparation of 1-(4-(trifluoromethyl)-2-morpholinobenzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Amine 2d (362 mg, 3.8 mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.12 g, 1equiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1b (384 mg, 2.56 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 200 mg of a pale rose solid. Yield = 18% 1HNMR (DMSO, 400 MHz) delta 2.91 (4H, m), 3.76 (4H, m), 4.46 (2H, d, J = 5.6 Hz), 6.97 (3H, m), 7.05 (1H, m), 7.36 (1H, s), 7.46 (1H, d), 7.54 (1H, d), 8.53 (1H, s), 11.00 (1H, bs); [M+1] 437.1 (C20H19F3N4O4 requires 436.4).).

Reference：
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Analyzing the synthesis route of 4-Aminobenzo[d]oxazol-2(3H)-one

The chemical industry reduces the impact on the environment during synthesis,81900-93-8,4-Aminobenzo[d]oxazol-2(3H)-one,I believe this compound will play a more active role in future production and life.

Commercially available 2-chloro-4-trifluoromethylbenzylamine (572 mg, 2.7 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (809 mg, 2.7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound lb (270 mg, 1.8 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 70 mg of a white solid. Yield = 10% ‘HNMR (DMSO, 400 MHz) delta 4.45 (2H, d, J = 6 Hz), 6.97 (2H, d, J = 4.4 Hz), 7.07 (2H, m), 7.63 (1H, d, J = 8 Hz), 7.74 (2H, d), 7.86 (1H, s), 8.61 (1H, bs), 10.90 (1H, bs); [M+1] 386.6 (C16H11CIF3N3O3 requires 385.7).

New learning discoveries about 81900-93-8

It is a common heterocyclic compound, the benzoxazole compound, 4-Aminobenzo[d]oxazol-2(3H)-one, cas is 81900-93-8 its synthesis route is as follows.

Commercially available 4-trifluoromethylbenzylamine (0.5 ml, 3.5 mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1 g, 3.5 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound lb (350 mg, 2.33 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 9.5 / MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 200 mg of a white solid. Yield = 24% ‘HNMR (DMSO, 400 MHz) delta 4.41 (2H, d, J = 6 Hz), 6.98 (3H, m), 7.05 (1H, m), 7.55 (2H, d), 7.70 (2H, d, J = 8 Hz), 8.49 (1H, bs), 1 1.00 (1H, bs); [M+1] 352.1 (C16H12F3N3O3 requires 351.28).

Some tips on 81900-93-8

It is a common heterocyclic compound, the benzoxazole compound, 4-Aminobenzo[d]oxazol-2(3H)-one, cas is 81900-93-8 its synthesis route is as follows.

Amine 2a (1.2 g, 5.5 mmol) (Scheme 7) was dissolved in 40ml of AcOEt and at 0C triphosgene (1.63 g, 5.5 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound lb (820 mg, 5.5 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 7 / petroleum ether 3). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 3 0ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 300 mg of a white solid. Yield = 14% ‘HNMR (DMSO, 200 MHz) delta 2.51 (6H, s), 4.71 (2H, d, J = 5.6 Hz), 6.55 (2H, d, J = 8.2 Hz), 7.05 (IH, t, J = 7.6 Hz), 7.40 (IH, m), 7.51 (IH, d), 10.06 (IH, bt), 1 1.53 (IH, bs), 1 1.80 (IH, bs); [M+1] 395.1 (C18H17F3N4O3 requires 394.35).

The important role of 81900-93-8

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 4-Aminobenzo[d]oxazol-2(3H)-one, and cas is 81900-93-8, its synthesis route is as follows.

Example 27: 1-(4-fluoro-2-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea (scheme 1) Preparation of 1-(4-fluoro-2-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Commercially available 4-fluoro-2-trifluoromethylbenzylamine (0.5 ml, 3.7 mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.12 g, 3.7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5ml) of compound 1b (360 mg, 2.4 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 4 / petroleum ether 6). The solvent was evaporated and the crude was dissolved in AcOEt (30ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 90 mg of a white solid. Yield = 10% 1HNMR (DMSO, 200 MHz) delta 4.36 (2H, d, J = 5.6 Hz), 6.71 (1H, t, J = 6 Hz), 6.98 (2H, m), 7.56 (4H, m), 8.55(1H, bs), 11.09 (1H, bs); [M+1] 370.2 (C16H11F4N3O3 requires 369.27).

Reference：
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

The important role of 81900-93-8

Name is 4-Aminobenzo[d]oxazol-2(3H)-one, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 81900-93-8, its synthesis route is as follows.

Commercially available 2-fluoro-4-trifluoromethylbenzylamine (0.5 ml, 3.7 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (1.12 g, 3.7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added drop wise to a solution in DMF (5 ml) of compound lb (360 mg, 2.4 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 100 mg of a white solid. Yield = 1 1 % ‘HNMR (DMSO, 400 MHz) delta 4.43 (2H, d, J = 6 Hz), 6.99 (3H, m), 7.05 (1H, m), 7.62 (3H, m), 8.53 (1H, bs), 10.98 (1H, bs); [M+1] 370.1 (C 16H1 1F4N3O3 requires 369.27).

Some tips on 4-Aminobenzo[d]oxazol-2(3H)-one

Name is 4-Aminobenzo[d]oxazol-2(3H)-one, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 81900-93-8, its synthesis route is as follows.

1854.96 kg of 99.1% pure 4-amino-2-benzoxazolone (V) 763.2 kg of isopropanol, 9274.8 kg of ethyl acetate, 10500 kg of sulfuric acid, 869.8 kg of sodium nitrite, 12.1 kg of copper(II) sulfate were mixed and stirred. The temperature was raised until the end of the reaction; the layer was allowed to stand, and ethyl acetate was distilled off to obtain 1544.6 kg of 2-benzoxazolone (VI) having a purity of 99.3% in a yield of 92.7%.

Reference：
Patent; Shao Yutian; (12 pag.)CN110156712; (2019); A;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Some tips on 81900-93-8

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 4-Aminobenzo[d]oxazol-2(3H)-one, and cas is 81900-93-8, its synthesis route is as follows.

Amine 2d (362 mg, 3.8 mmol) (Scheme 7) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.12 g, l equiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound lb (384 mg, 2.56 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 200 mg of a pale rose solid. Yield = 18% ‘HNMR (DMSO, 400 MHz) delta 2.91 (4H, m), 3.76 (4H, m), 4.46 (2H, d, J = 5.6 Hz), 6.97 (3H, m), 7.05 (1H, m), 7.36 (1H, s), 7.46 (1H, d), 7.54 (1H, d), 8.53 (1H, s), 1 1.00 (1H, bs); [M+1] 437.1 (C2oH19F3N4O4 requires 436.4).