Dimethylformamide → HCID 18182333, compound

HRID 1359415Notes

Reaction equation

HRID 1359415 reaction equation
[Br:1]N1C(=O)CCC1=O.CN(C)C=O.[CH2:14]([C:21]1[C:22]2[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][C:23]=2[S:24][CH:25]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[Br:1][C:25]1[S:24][C:23]2[CH2:26][CH:27]([CH2:30][OH:31])[CH2:28][CH2:29][C:22]=2[C:21]=1[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 18182277HCID 18182277, compound

Product 1

HCID 18182333HCID 18182333, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

103 mg of N-bromosuccinimide was added little by little to a solution of 5.0 ml of N,N-dimethylformamide containing 136 mg of 3-benzyl-6-(hydroxymethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene under ice-cooling. After stirring for one hour, water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic phase was washed with water and brine, and the solvent was removed. Then, the residue was subjected to silica gel column chromatography and eluted with hexane and then with hexane/ethyl acetate (2:1), to give 164 mg of the target compound.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. customthe solvent was removed
  5. washeluted with hexane

Sources & evidence

ORD record
ord-be9a5c15e47d4940873b75586d1ef72f
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

Loading…