Dimethylformamide → HCID 14373007, compound

HRID 847280Notes

Reaction equation

HRID 847280 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 2.0 g of ethyl mercaptoacetate, 3.13 g of 1-bromo-3-chloropropane, 2.29 g of anhyrous potassium carbonate and 10 ml of 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 and water in order, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was applied to silica gel column chromatography and eluted with a mixture of hexane-ethyl acetate (15:1) to obtain 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 and water in order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with a mixture of hexane-ethyl acetate (15:1)

Sources & evidence

ORD record
ord-d91eedffe96b477c85a5f9416be891ec
Source dataset
uspto-grants-1992_08
Patent number
US05140046

Reaction notes

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