Water → (+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbothiohydrazide

HRID 25058Notes

Reaction equation

HRID 25058 reaction equation
[CH3:1][CH:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[N:4][N:3]1[C:25](Cl)=[S:26].O.[NH2:29][NH2:30].O>O1CCCC1>[CH3:1][CH:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[N:4][N:3]1[C:25](=[S:26])[NH:29][NH2:30]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 12137404(+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbothioyl chloride

Product 1

HCID 12137411(+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbothiohydrazideYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g (2.47 mmol) of carbothioyl chloride XI was added to a stirred solution of 0.37 g (7.42 mmol) of hydrazine hydrate in 15 ml of tetrahydrofuran at 5-10° C. over a period of about 0.5 h, then after 1 h stirring, the mixture was poured into water and the precipitated product was filtered off to yield 0.89 g (90%) of the crude product. After drying, it was used in the further reaction steps. The melting point of the product after recrystallization from ethanol was 196° C.

Workup

  1. filtrationthe precipitated product was filtered off

Sources & evidence

ORD record
ord-6c8e13b14b354cb7840c0e0e8f5d4e6f
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Reaction notes

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