Dimethylformamide → HCID 54551865, compound

HRID 223178Notes

Reaction equation

HRID 223178 reaction equation
[CH:1]1[N:2]=[CH:3][N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=[O:15])[N:7]3[CH2:16][CH2:17][C@H:6]3[C:5]=12.[Cl:18]N1C(=O)CCC1=O.CN(C)C=O>O>[Cl:18][C:1]1[N:2]=[CH:3][N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=[O:15])[N:7]3[CH2:16][CH2:17][C@H:6]3[C:5]=12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 70485483HCID 70485483, compound

Product 1

HCID 54551865HCID 54551865, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.54 g (2.4 mmol) of (S)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one and 0.32 g (2.4 mmol) of N-chlorosuccinimide are treated with 10 ml of dimethylformamide and the mixture is stirred at 90° for 40 minutes. The mixture is poured into 50 ml of water and extracted four times with chloroform. The combined chloroform extracts are washed three times with water, dried over magnesium suphate and evaporated. The crude product is chromatographed on silica gel using chloroform/methanol (19:1) for the elution and subsequently recrystallized from ethyl acetate. There is obtained (S)-1-chloro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of melting point 210°-214°.

Workup

  1. extractionextracted four times with chloroform
  2. washThe combined chloroform extracts are washed three times with water
  3. dry with materialdried over magnesium suphate
  4. customevaporated
  5. customThe crude product is chromatographed on silica gel
  6. washfor the elution
  7. customsubsequently recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-08b19252fceb46209ac043ede2051f5c
Source dataset
uspto-grants-1982_10
Patent number
US04352816

Reaction notes

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