2,4-dimethylbenzohydrazide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 2,4-dimethylbenzoate (2 g, 12.2 mmol) in MeOH (10 mL) was added anhydrous hydrazine (1.95 mL, 61 mmol) and the mixture was heated under reflux for 40 hours. Then the mixture was evaporated and dried under vacuum to give 2,4-dimethylbenzohydrazide as a white solid (2 g, 100%; MS (M+H, 165). the mixture was heated under reflux for 40 hours Then the mixture was evaporated dried under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,4-dimethylbenzohydrazide (example 16b) (2 g) in dry dioxane (12 mL) was added cyanic bromide (1.28 g, 12.2 mmol) followed by a solution of NaHCO3 (1.02 g, 12.2 mmol) in water (12 mL). The resulting mixture was stirred 2 hours at rt. The solution was concentrated to ½ volume on vacuum and diluted with water (20 mL). The resulting solid was collected and dried on vacuum to give 5-(2,4-Dimethylphenyl)-1,3,4-oxadiazol-2-amine (1.88 g, 82%) as a white solid. 1H NMR (300 MHz, dMSO): δ 2.29 (s, 3H), 2.52 (d, 3H), 7.13 (d, 1H), 7.16 (s, 3H), 7.54-7.56 (d, 1H); MS (M+H, 190). The solution was concentrated diluted with water (20 mL) The resulting solid was collected dried on vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 2,4-dimethylbenzoate (2 g, 12.2 mmol) in MeOH (10 mL) was added anhydrous hydrazine (1.95 mL, 61 mmol) and the mixture was heated under reflux for 40 hours. Then the mixture was evaporated and dried under vacuum to give 2,4-dimethylbenzohydrazide as a white solid (2 g, 100%; MS (M+H, 165). the mixture was heated under reflux for 40 hours Then the mixture was evaporated dried under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,4-dimethylbenzohydrazide (example 16b) (2 g) in dry dioxane (12 mL) was added cyanic bromide (1.28 g, 12.2 mmol) followed by a solution of NaHCO3 (1.02 g, 12.2 mmol) in water (12 mL). The resulting mixture was stirred 2 hours at rt. The solution was concentrated to ½ volume on vacuum and diluted with water (20 mL). The resulting solid was collected and dried on vacuum to give 5-(2,4-Dimethylphenyl)-1,3,4-oxadiazol-2-amine (1.88 g, 82%) as a white solid. 1H NMR (300 MHz, dMSO): δ 2.29 (s, 3H), 2.52 (d, 3H), 7.13 (d, 1H), 7.16 (s, 3H), 7.54-7.56 (d, 1H); MS (M+H, 190). The solution was concentrated diluted with water (20 mL) The resulting solid was collected dried on vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 2,4-dimethylbenzoate (2 g, 12.2 mmol) in MeOH (10 mL) was added anhydrous hydrazine (1.95 mL, 61 mmol) and the mixture was heated under reflux for 40 hours. Then the mixture was evaporated and dried under vacuum to give 2,4-dimethylbenzohydrazide as a white solid (2 g, 100%; MS (M+H, 165). the mixture was heated under reflux for 40 hours Then the mixture was evaporated dried under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,4-dimethylbenzohydrazide (example 16b) (2 g) in dry dioxane (12 mL) was added cyanic bromide (1.28 g, 12.2 mmol) followed by a solution of NaHCO3 (1.02 g, 12.2 mmol) in water (12 mL). The resulting mixture was stirred 2 hours at rt. The solution was concentrated to ½ volume on vacuum and diluted with water (20 mL). The resulting solid was collected and dried on vacuum to give 5-(2,4-Dimethylphenyl)-1,3,4-oxadiazol-2-amine (1.88 g, 82%) as a white solid. 1H NMR (300 MHz, dMSO): δ 2.29 (s, 3H), 2.52 (d, 3H), 7.13 (d, 1H), 7.16 (s, 3H), 7.54-7.56 (d, 1H); MS (M+H, 190). The solution was concentrated diluted with water (20 mL) The resulting solid was collected dried on vacuum