Acetone → 2-(2-Chloroethyl thio)-1-methylimidazole

HRID 1654167Notes

Reaction equation

HRID 1654167 reaction equation
CC(C)=O.[SH:5][C:6]1[N:7]([CH3:11])[CH:8]=[CH:9][N:10]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][Cl:21]>C(Cl)Cl>[Cl:21][CH2:20][CH2:19][S:5][C:6]1[N:7]([CH3:11])[CH:8]=[CH:9][N:10]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 178480602HCID 178480602, compound

Product 1

HCID 200795872-(2-Chloroethyl thio)-1-methylimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an acetone (40 ml) solution containing 2-mercapto-1-methylimidazole (4.0 g ) and anhydrous potassium carbonate (20 g) was added dropwise, under ice-cooling, 1-bromo-2-chloroethane (5.0 ml). The mixture was stirred for 2 hours at room temperature, to which was added methylene chloride (40 ml), followed by filtration. The filtrate was concentrated under reduced pressure to give 2-(2-chloroethyl thio)-1-methylimidazole (6.2 g ) as a colorless oily substance.

Workup

  1. additionwas added dropwise, under ice-
  2. temperaturecooling
  3. filtrationfollowed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bcb4c48ca09c403f84f1d6b9719ff0bd
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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