Thionyl Chloride → N-(2-chloroethyl)-N-methyl-1-pyrrolidinecarboxamide

HRID 2248620Notes

Reaction equation

HRID 2248620 reaction equation
O[CH2:2][CH2:3][N:4]([CH3:12])[C:5]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6].S(Cl)([Cl:15])=O>CN(C)C=O.CC1C=CC=CC=1>[Cl:15][CH2:2][CH2:3][N:4]([CH3:12])[C:5]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 15078442N-(2-hydroxyethyl)-N-methyl-1-pyrrolidinecarboxamide

Product 1

HCID 15078443N-(2-chloroethyl)-N-methyl-1-pyrrolidinecarboxamideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of 4 parts of N-(2-hydroxyethyl)-N-methyl-1-pyrrolidinecarboxamide in 22.5 parts of methylbenzene were added 2.9 parts of thionyl chloride. After the addition of a few drops of N,N-dimethylformamide, the reaction mixture was heated slowly to reflux temperature. After stirring for 2 hours at this temperature, the mixture was cooled and the whole was evaporated, yielding 4.5 parts (100%) of N-(2-chloroethyl)-N-methyl-1-pyrrolidinecarboxamide as a residue (int. 31).

Workup

  1. temperaturethe reaction mixture was heated slowly
  2. temperatureto reflux temperature
  3. temperaturethe mixture was cooled
  4. customthe whole was evaporated

Sources & evidence

ORD record
ord-8b0080b0d6cd4321b5458decae8b346c
Source dataset
uspto-grants-1991_08
Patent number
US05041454

Reaction notes

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