Water → HCID 53655027, compound

HRID 223222Notes

Reaction equation

HRID 223222 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][CH:14]=[C:10]3[C@@H:9]3[CH2:15][CH2:16][CH2:17][N:8]3[C:7](=[O:18])[C:6]=2[CH:19]=1.[Cl:20]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:20][C:14]1[N:13]=[CH:12][N:11]2[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:19][C:6]=3[C:7](=[O:18])[N:8]3[CH2:17][CH2:16][CH2:15][C@H:9]3[C:10]=12

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 54105642HCID 54105642, compound

Product 1

HCID 53655027HCID 53655027, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3 g (11 mmol) of (S)-7-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one in 30 ml of dimethylformamide are stirred at 90° for 30 minutes with 1.60 g of N-chlorosuccinimide. The solution is poured into water and extracted with chloroform. The chloroform extracts are washed several times with water, dried over magnesium sulphate and evaporated. By chromatography on a silica gel column and subsequent recrystallization from ethyl acetate there is obtained (S)-1,7-dichloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 209°-210°.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform extracts are washed several times with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customBy chromatography on a silica gel column and subsequent recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-670758ee544147dca092b6627d31fe71
Source dataset
uspto-grants-1982_10
Patent number
US04352818

Reaction notes

Loading…