Hydrogen Sulfide → HCID 86753953, compound

HRID 1737350Notes

Reaction equation

HRID 1737350 reaction equation
[SH2:1].[O:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]2[CH:14]=[N:15][C:16]([C:17]#[N:18])=[C:6]2[C@@H:5]2[CH2:19][CH2:20][N:4]12>N1C=CC=CC=1.C(N(CC)CC)C>[O:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]2[CH:14]=[N:15][C:16]([C:17](=[S:1])[NH2:18])=[C:6]2[C@@H:5]2[CH2:19][CH2:20][N:4]12

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 54516569HCID 54516569, compound

Product 1

HCID 86753953HCID 86753953, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

A stream of hydrogen sulphide was conducted for 1/2 hr. through a solution of 5.0 g (0.020 mol) of (S)-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile in 100 ml of pyridine and 1 ml of triethylamine. The dark brown solution was left to stand for 70 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 extracted. The pale yellow product was chromatographed over silica gel with ethyl acetate as the eluent, stirred vigorously in ether for 16 hrs. and subsequently filtered off under suction. There were obtained 3.8 g (67%) of (S)-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-thiocarboxamide as pale yellow crystals; m.p. 227-230° and [α]D20 =-473.7° (DMF, c=1%).

Workup

  1. waitThe dark brown solution was left
  2. custom, then de-gassed with a stream of nitrogen
  3. customThe residue was partitioned between dichloromethane and water
  4. extractionextracted
  5. customThe pale yellow product was chromatographed over silica gel with ethyl acetate as the eluent
  6. filtrationand subsequently filtered off under suction

Sources & evidence

ORD record
ord-4cede98676ad49e3bbb21941de8abb5f
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

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