Hydrogen Sulfide → HCID 21842257, compound

HRID 1737377Notes

Reaction equation

HRID 1737377 reaction equation
[SH2:1].[Cl:2][C:3]1[C:8]2[C:9](=[O:20])[N:10]([CH3:19])[CH2:11][C:12]3[N:13]([CH:14]=[N:15][C:16]=3[C:17]#[N:18])[C:7]=2[CH:6]=[CH:5][C:4]=1[F:21]>N1C=CC=CC=1.C(N(CC)CC)C>[Cl:2][C:3]1[C:8]2[C:9](=[O:20])[N:10]([CH3:19])[CH2:11][C:12]3[N:13]([CH:14]=[N:15][C:16]=3[C:17](=[S:1])[NH2:18])[C:7]=2[CH:6]=[CH:5][C:4]=1[F:21]

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 218422677-chloro-8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile

Product 1

HCID 21842257HCID 21842257, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

A stream of hydrogen sulphide was conducted for 1/2 hr. through a solution of 3.0 g (0.0103 mol) of 7-chloro-8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile in 10 ml of pyridine and 1.0 ml of triethylamine. The green solution was left to stand for 64 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 2.45 g (73%) of 7-chloro-8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-thiocarboxamide.

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-88cca217163941d2b0386f39574aeb5f
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

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