Hydrochloric Acid → (S)-8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-thiocarboxamide

HRID 867541Notes

Reaction equation

HRID 867541 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]3[CH2:20][CH2:19][CH2:18][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[N:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N)(=[S:24])C.Cl.[OH-].[Na+]>O.CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]3[CH2:20][CH2:19][CH2:18][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](=[S:24])[NH2:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723949ThioacetamideHCID 54287641(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile

Product 1

HCID 53664939(S)-8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-thiocarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

20.0 g (67 mmol) of (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile and 10.06 g (134 mmol) of thioacetamide are heated to 90° together with 100 ml of dry N,N-dimethylformamide, whereupon the mixture is saturated with dry hydrogen chloride at this temperature for 5 hours. The mixture is cooled to room temperature and poured into 2.5 l of water. The mixture is neutralized to pH 7 with sodium hydroxide solution and the precipitated product is filtered off under suction. The material on the suction filter is taken up in methylene chloride, insoluble material is filtered off and the filtrate is washed with water, dried over magnesium sulphate and concentrated in half. By suction filtration and recrystallization from ethyl acetate there is obtained (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbothioamide of melting point 247°-248°.

Workup

  1. filtrationthe precipitated product is filtered off under suction
  2. filtrationThe material on the suction filter
  3. filtrationinsoluble material is filtered off
  4. washthe filtrate is washed with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in half
  7. filtrationBy suction filtration and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-010ef6def8a042bbb7fd7fb782719940
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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