Dimethyl Sulfoxide → HCID 15307547, compound

HRID 1493454Notes

Reaction equation

HRID 1493454 reaction equation
[C:1]1([CH:7]2[CH2:11][NH:10][C:9](=[O:12])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:13].[K+].CS(C)=[O:17].[CH2:19]([O:21][C:22](=[O:25])[CH2:23]Cl)[CH3:20].[C:26]1([CH3:32])C=CC=CC=1>O>[C:20]([CH2:19][O:21][C:22](=[O:25])[CH2:23][N:10]1[CH2:11][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][C:9]1=[O:12])([O:17][CH2:26][CH3:32])=[O:13]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 1140TolueneHCID 7751Ethyl chloroacetateHCID 14797Potassium HydroxideHCID 1213974-Phenyl-2-pyrrolidinone

Product 1

HCID 15307547HCID 15307547, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 80.5 g (0.5 mol) of 4-phenyl-2-pyrrolidone, 70 g (1.25 mol) of potassium hydroxide, 500 ml of dimethylsulphoxide and 150 ml of toluene are heated at reflux under stirring at the reaction mixture temperature of 130° C. till a complete dispergation of the alkali, whereafter the mixture is dropwise added with 153 g (1.25 mol) of ethylchloroacetate and allowed to stand at room temperature for one day. The mixture is diuted with 1.2 l of water and extracted twice with 100 ml portions of toluene; the extracts are subjected to fractionation to give 73.2 g (47%) of (2-oxo-4-phenyl-1-pyrrolidinyl)acetic acid carboethoxymethyl ester, b.p. 210°-214° C. (1 mm Hg), nD20 =1.5212.

Workup

  1. temperatureare heated
  2. temperatureat reflux
  3. extractionextracted twice with 100 ml portions of toluene

Sources & evidence

ORD record
ord-fe1f4a09504146b58b8392d72a76e6c3
Source dataset
uspto-grants-1991_06
Patent number
US05021568

Reaction notes

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