Ethyl chloroacetate → HCID 23315294, compound

HRID 745230Notes

Reaction equation

HRID 745230 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[N:11]([C:12](=[O:14])[CH3:13])[CH2:10][CH2:9][NH:8][C:7]1=[O:15].[CH2:16]([O:18][C:19](=[O:22])[CH2:20]Cl)[CH3:17]>CS(C)=O>[C:19]([CH2:20][N:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:14])[CH3:13])[CH:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[C:7]1=[O:15])([O:18][CH2:16][CH3:17])=[O:22]

Participants

4

Reactant 2

HCID 7751Ethyl chloroacetateHCID 13120674HCID 13120674, compound

Product 1

HCID 23315294HCID 23315294, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

12 g (0.053 mol) of 3-(2-thienyl)-4-acetylpiperazin-2-one, prepared in accordance with Example 17, are stirred with 6.6 g (0.059 mol) of potassium tert.-butylate in 100 ml of dimethyl sulphoxide. After removing 10 ml of dimethyl sulphoxide by distillation in vacuo, 6.4 g (0.059 mol) of ethylchloroacetate are added dropwise at room temperature and the mixture is stirred for a further 12 hours. The dimethyl sulphoxide is removed by evaporation in vacuo, the residue is stirred with water and taken up in ethyl acetate, and the organic phase is separated off. Distilling off the ethyl acetate gives 13.8 g of the title product, 88% of theory (molecular weight 296), in the form of a viscous oil.

Workup

  1. customAfter removing 10 ml of dimethyl sulphoxide
  2. additionare added dropwise at room temperature
  3. customThe dimethyl sulphoxide is removed by evaporation in vacuo
  4. stirringthe residue is stirred with water
  5. customthe organic phase is separated off
  6. distillationDistilling off the ethyl acetate

Sources & evidence

ORD record
ord-d188686654c64156a8839444dc4f25c7
Source dataset
uspto-grants-1986_07
Patent number
US04598079

Reaction notes

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