Hydrogen Sulfide → HCID 21842253, compound

HRID 1737370Notes

Reaction equation

HRID 1737370 reaction equation
[SH2:1].[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]3[CH:13]=[N:14][C:15]([C:16]#[N:17])=[C:11]3[CH2:10][N:9]([CH3:18])[C:8](=[O:19])[C:7]=2[CH:20]=1>N1C=CC=CC=1.C(N(CC)CC)C>[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]3[CH:13]=[N:14][C:15]([C:16](=[S:1])[NH2:17])=[C:11]3[CH2:10][N:9]([CH3:18])[C:8](=[O:19])[C:7]=2[CH:20]=1

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 98815428-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile

Product 1

HCID 21842253HCID 21842253, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

A stream of hydrogen sulphide was conducted for 1/2 hr. through a solution of 4.4 g (0.0172 mol) of 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile in 100 ml of pyridine and 1 ml of triethylamine. The dark 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/tetrahydrofuran and water, extracted, concentrated, stirred vigorously in ether and filtered off under suction. There were obtained 4.55 g (91%) of 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-thiocarboxamide as yellow crystals.

Workup

  1. waitThe dark green solution was left
  2. custom, then de-gassed with a stream of nitrogen
  3. customThe residue was partitioned between dichloromethane/tetrahydrofuran and water
  4. extractionextracted
  5. concentrationconcentrated
  6. filtrationfiltered off under suction

Sources & evidence

ORD record
ord-751a7dbc632f406a823bb92ada4676ea
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

Loading…