tert-butyl N-(benzylideneamino)carbamate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of N'-benzylidenehydrazinecarboxylic acid tert-butyl ester (2.7 g, 12.3 mmol) in tetrahydrofuran (100 ml) was added 10% palladium on carbon (0.3 g) and the mixture was hydrogenated with 280 ml of hydrogen for 40 min at atmospheric pressure. The mixture was filtered through a plug of celite and the filtrate was concentrated in vacuo to give 2.63 g of N'-benzylhydrazinecarboxylic acid tert-butyl ester. The mixture was filtered through a plug of celite the filtrate was concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of t-butyl carbazate (2.0 g, 15.1 mmol) in 99% ethanol (20 ml) was added benzaldehyde (1.6 g, 15.1 mmol) and the mixture was stirred for 30 min. Then the mixture was cooled to 0° C. and the precipitate was separated and washed with cold ethanol and dried in vacuo to give 2.7 g (81%) of N'-benzylidenehydrazinecarboxylic acid tert-butyl ester. the precipitate was separated washed with cold ethanol dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of t-butyl carbazate (5.62 g, 42.5 mmol) in ethyl acetate (15 mL) was added with stirring benzaldehyde (4.51 g, 42.5 mmol). Crystallization occurred and the resulting slurry was stirred at rt for 45 min. Hexanes (70 mL) was added and the slurry was cooled to 0° C. The slurry was stirred at 0° C. for 60 min, then filtered and rinsed with cold hexanes (20 mL) and dried in vacuo at 40° C. to afford the title compound as a solid (8.34 g, 89.0%): mp 184.1-184.9° C.; 1H NMR (DMSO-d6) δ 10.91 (s, 1H), 7.99 (s, 1H), 7.58 (d, 2H, J=3 Hz), 7.39 (m, 3H), 1.45 (s, 9H); 13C NMR (DMSO-d6) δ 153.0, 143.8, 135.3, 130.0, 129.4, 127.2, 80.1, 28.8; IR (KBr mull) 2983, 1735, 1511, 1157 cm−1; A portion was recrystallized (ethyl acetate) for analysis. Anal. Calcd. For C12H16N2O2: C, 65.43; H, 7.32; N, 12.72. Found: C, 65.16; H, 7.43; N, 12.62. Crystallization Hexanes (70 mL) was added the slurry was cooled to 0° C The slurry was stirred at 0° C. for 60 min filtered rinsed with cold hexanes (20 mL) dried in vacuo at 40° C.

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

Procedure: To a solution of t-butyl carbazate (5.62 g, 42.5 mmol) in ethyl acetate (15 mL) was added with stirring benzaldehyde (4.51 g, 42.5 mmol). Crystallization occurred and the resulting slurry was stirred at rt for 45 min. Hexanes (70 mL) was added and the slurry was cooled to 0° C. The slurry was stirred at 0° C. for 60 min, then filtered and rinsed with cold hexanes (20 mL) and dried in vacuo at 40° C. to afford the title compound as a solid (8.34 g, 89.0%): mp 184.1-184.9° C.; 1H NMR (DMSO-d6) δ 10.91 (s, 1H), 7.99 (s, 1H), 7.58 (d, 2H, J=3 Hz), 7.39 (m, 3H), 1.45 (s, 9H); 13C NMR (DMSO-d6) δ 153.0, 143.8, 135.3, 130.0, 129.4, 127.2, 80.1, 28.8; IR (KBr mull) 2983, 1735, 1511, 1157 cm−1; A portion was recrystallized (ethyl acetate) for analysis. Anal. Calcd. For C12H16N2O2: C, 65.43; H, 7.32; N, 12.72. Found: C, 65.16; H, 7.43; N, 12.62. Crystallization Hexanes (70 mL) was added the slurry was cooled to 0° C The slurry was stirred at 0° C. for 60 min filtered rinsed with cold hexanes (20 mL) dried in vacuo at 40° C.

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

Procedure: To a solution of N′-benzylidenehydrazinecarboxylic acid tert-butyl ester (2.7 g, 12.3 mmol) in tetrahydrofuran (100 ml) was added 10% palladium on carbon (0.3 g) and the mixture was hydrogenated with 280 ml of hydrogen for 40 min at atmospheric pressure. The mixture was filtered through a plug of celite and the filtrate was concentrated in vacuo to give 2.63 9 of N′-benzylhydrazinecarboxylic acid tert-butyl ester. The mixture was filtered through a plug of celite the filtrate was concentrated in vacuo

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

Procedure: To a solution of N′-benzylidenehydrazinecarboxylic acid tert-butyl ester (2.7 g, 12.3 mmol) in tetrahydrofuran (100 ml) was added 10% palladium on carbon (0.3 g) and the mixture was hydrogenated with 280 ml of hydrogen for 40 min at atmospheric pressure. The mixture was filtered through a plug of celite and the filtrate was concentrated in vacuo to give 2.63 9 of N′-benzylhydrazinecarboxylic acid tert-butyl ester. The mixture was filtered through a plug of celite the filtrate was concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of t-butyl carbazate (2.0 g, 15.1 mmol) in 99% ethanol (20 ml) was added benzaldehyde (1.6 g, 15.1 mmol) and the mixture was stirred for 30 min. Then the mixture was cooled to 0° C. and the precipitate was separated and washed with cold ethanol and dried in vacuo to give 2.7 g (81%) of N′-benzylidenehydrazinecarboxylic acid tert-butyl ester. the precipitate was separated washed with cold ethanol dried in vacuo

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

Procedure: ##STR185## To a solution of N'-benzylidenehydrazinecarboxylic acid tert-butyl ester (2.7 g, 12.3 mmol) in tetrahydrofuran (100 ml) was added 10% palladium on carbon (0.3 g) and the mixture was hydrogenated with 280 ml of hydrogen for 40 min at atmospheric pressure. The mixture was filtered through a plug of celite and the filtrate was concentrated in vacuo to give 2.63 g of N'-benzylhydrazinecarboxylic acid tert-butyl ester. The mixture was filtered through a plug of celite the filtrate was concentrated in vacuo