Ethanol → HCID 86700963, compound

HRID 339604Notes

Reaction equation

HRID 339604 reaction equation
S(Cl)(Cl)=O.[O:5]=[C:6]1[CH:10]([C:11]([OH:13])=[O:12])[CH2:9][CH2:8][N:7]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:20](O)[CH3:21]>>[O:5]=[C:6]1[CH:10]([C:11]([O:13][CH2:20][CH3:21])=[O:12])[CH2:9][CH2:8][N:7]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 30437622-Oxo-1-phenylpyrrolidine-3-carboxylic acid

Product 1

HCID 86700963HCID 86700963, compoundYield 79%

Conditions

Temperature
80 °C

Procedure

Thionyl chloride is added at 0° C. (5.8 g) to a solution of 2-oxo-1-phenylpyrrolidine-3-carboxylic acid (5 g) in ethanol, and the batch is stirred at 80° C. for 4 h. When the reaction is complete, the batch is concentrated in vacuo, the residue is taken up in water and extracted with ethyl acetate. The organic phase is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution and dried over sodium sulfate, giving ethyl 2-oxo-1-phenylpyrrolidine-3-carboxylate (4.5 g, 79%);

Workup

  1. concentrationthe batch is concentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-0bb585ce4b9e4890bac05b1936a9b8a1
Source dataset
uspto-grants-2014_11
Patent number
US08895535B2

Reaction notes

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