Water → HCID 54423540, compound

HRID 223225Notes

Reaction equation

HRID 223225 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][CH2:18][C@H:6]3[C:5]=12.[Br:19]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:19][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][CH2:18][C@H:6]3[C:5]=12

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 54051837HCID 54051837, compound

Product 1

HCID 54423540HCID 54423540, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.5 g (10.4 mmol) of (S)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one in 20 ml of dimethylformamide are stirred at room temperature for 30 minutes with 1.86 g (10.4 mmol) of N-bromosuccinimide. 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. After two-fold recrystallization from ethyl acetate, there is obtained (S)-1-bromo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 225°-226°.

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. customAfter two-fold recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-3a52d11b05c745ad9df2a13e0366c754
Source dataset
uspto-grants-1982_10
Patent number
US04352818

Reaction notes

Loading…