Hydrogen Sulfide → HCID 21842269, compound

HRID 1418928Notes

Reaction equation

HRID 1418928 reaction equation
[SH2:1].[CH3:2][N:3]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]2[CH:15]=[N:16][C:17]([C:18]#[N:19])=[C:5]2[CH2:4]1>N1C=CC=CC=1.C(N(CC)CC)C>[CH3:2][N:3]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]2[CH:15]=[N:16][C:17]([C:18](=[S:1])[NH2:19])=[C:5]2[CH2:4]1

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 139845425-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile

Product 1

HCID 21842269HCID 21842269, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

A stream of hydrogen sulphide was passed for 1 hr. through a solution of 10.2 g (0.429 mol) of 5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile in 250 ml of pyridine and 2.5 ml of triethylamine. The green solution was left to stand for 48 hrs., then de-gassed with a stream of nitrogen and subsequently completely freed from the solvents. The residue was partitioned between dichloromethane and water and the suspension obtained was suction filtered. There were obtained 9.0 g (87%) of 5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-thiocarboxamide as yellow crystals. A sample was recrystallized from methanol and gave pale yellow crystals; m.p. 295°-297°.

Workup

  1. waitThe green solution was left
  2. custom, then de-gassed with a stream of nitrogen
  3. customThe residue was partitioned between dichloromethane and water
  4. customthe suspension obtained
  5. filtrationfiltered

Sources & evidence

ORD record
ord-1dc1e241b09a455390e3793bb0e3425a
Source dataset
uspto-grants-1999_03
Patent number
US05885986

Reaction notes

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