2-Pyrrolidone → HCID 14441091, compound

HRID 892730Notes

Reaction equation

HRID 892730 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.[Cl:7][CH2:8][CH2:9][N:10]=[C:11]=[O:12]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:7][CH2:8][CH2:9][NH:10][C:11]([N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])=[O:12]

Participants

4

Reactant 2

HCID 120252-PyrrolidoneHCID 160352-Chloroethyl isocyanate

Product 1

HCID 14441091HCID 14441091, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 21584019Toluene ethylacetateSolvent

Procedure

A mixture of 65.1 g (765 mmol) of 2-oxopyrrolidine and 67.3 g (638 mmol) of chloroethyl isocyanate was heated with stirring at 95°-105° C. overnight. After cooling, the reaction solution was refined by silica gel chromatography. The resulting compound obtained from the eluate with toluene-ethyl acetate (20/1-10/1 v/v) was recrystallized from CH2Cl2 -ether-n-hexane, whereby 107.7 g of the objective compound 1-(2-chloroethylcarbamoyl)-2-oxopyrrolidine (III-1) melting at 66.5°-67.5° C. was obtained as crystals.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. customwas recrystallized from CH2Cl2 -ether-n-hexane

Sources & evidence

ORD record
ord-ff8bcd1f15004b2b8e8ebd7457d674a8
Source dataset
uspto-grants-1992_06
Patent number
US05120733

Reaction notes

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