Dimethylformamide → HCID 14373007, compound

HRID 2107106Notes

Reaction equation

HRID 2107106 reaction equation
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[CH2:9][CH2:10][CH2:11][Cl:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C1(C)C=CC=CC=1>[Cl:12][CH2:11][CH2:10][CH2:9][S:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 12185Ethyl Thioglycolate

Product 1

HCID 14373007HCID 14373007, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.00 g of ethyl mercaptoacetate, 3.13 g of 1-bromo-3-chloropropane, 2.29 g of anhydrous potassium carbonate and 10 ml of N,N-dimethylformamide was stirred at room temperature for 3 hours. The reaction mixture was diluted with toluene and insoluble matters were filtered off. The filtrate was washed with an aqueous sodium hydroxide solution and water, in this sequence. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The residue was applied to silica gel column chromatography. Elution with a solvent mixture of hexane-ethyl acetate (15:1) gave 2.65 g of oily ethyl [(3-chloropropyl)thio]acetate.

Workup

  1. filtrationwere filtered off
  2. washThe filtrate was washed with an aqueous sodium hydroxide solution and water, in this sequence
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. washElution
  6. additionwith a solvent mixture of hexane-ethyl acetate (15:1)

Sources & evidence

ORD record
ord-9e5c1673521047b79ca5629787a7de17
Source dataset
uspto-grants-1990_06
Patent number
US04933348

Reaction notes

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