Water → 5-Benzylthiopentyl chloride

HRID 344240Notes

Reaction equation

HRID 344240 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:13].[CH2:14]([SH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH2:14]([S:21][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 960701-Bromo-5-chloropentane

Product 1

HCID 142211195-Benzylthiopentyl chlorideYield 54.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Potassium carbonate (5 g) and 1-bromo-5-chloropentane (4.9 g) were added to a solution of benzylmercaptan (3 g) in dimethylformamide (40 ml), and the mixture was stirred at 70-80° C. for 2 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure to give 3 g of 5-benzylthiopentyl chloride.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-eeef5c333f2f4c32ace74ee296174bc8
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

Loading…