Dimethylformamide → HCID 54075974, compound

HRID 1381601Notes

Reaction equation

HRID 1381601 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][SH:3].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[Cl-:19].[Cl-].[C:21]1([CH3:28])[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[Cl:19][CH2:28][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][S:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 22041937HCID 22041937, compound

Product 1

HCID 54075974HCID 54075974, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 1.22 g of ethyl thioglycolate, 1.4 g of anhydrous potassium carbonate and 20 ml of N,N-dimethylformamide was added 5.3 g of p-xylene dichloride followed by stirring at room temperature overnight. To the reaction mixture was added 50 ml of toluene. The mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was applied to silica gel column chromatography. Elution with a mixture of toluene-ethyl acetate (9:1) gave 1.61 g of oily ethyl [(p-chloromethylbenzyl)thio]acetate.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washElution
  5. additionwith a mixture of toluene-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-27c16b1190cd45e1944d8ebd52ad6189
Source dataset
uspto-grants-1989_02
Patent number
US04803211

Reaction notes

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