Hydrazine hydrate (1:1) → 2-hydrazino-5-phenyl-3H-1,4-benzodiazepine

HRID 1413364Notes

Reaction equation

HRID 1413364 reaction equation
[C:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][C:10](=S)[CH2:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:20][NH2:21]>CO>[C:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]([NH:20][NH2:21])[CH2:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 28029055-Phenyl-1,3-dihydro-2H-1,4-benzodiazepine-2-thione

Product 1

HCID 126123892-hydrazino-5-phenyl-3H-1,4-benzodiazepine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred mixture of 5-phenyl-1,3-dihydro-2H-1,4-benzodiazepine-2-thione (7.45 g., 0.03 mole) in methanol (300 ml.) was allowed to react with hydrazine hydrate (6.0 g., 0.12 mole) to give 5-phenyl-3H-1,4-benzodiazepin-2-yl hydrazine as an oil. A solution of thio material in tetrahydrofuran (75 ml.) was cooled in an ice bath and treated with a solution of chloroacetyl chloride (3.39 g., 0.03 mole) in tetrahydrofuran (25 ml.) to give 6.43 g. of chloroacetic acid, 2-(5-phenyl-3H-1,4-benzodiazepin-2-yl) hydrazide (A).

Sources & evidence

ORD record
ord-aaddeba4606449c8bb9f89290fd224a6
Source dataset
uspto-grants-1981_02
Patent number
US04250094

Reaction notes

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