Cyclohexyl isocyanate → N-(cyclohexyl)-N'-(2-chloroethyl)imidazolidinone

HRID 235990Notes

Reaction equation

HRID 235990 reaction equation
[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16]OC1=O.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[CH:1]1([N:7]2[CH2:16][CH2:17][N:13]([CH2:12][CH2:11][Cl:10])[C:8]2=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 18502Cyclohexyl isocyanateHCID 756333-(2-Chloroethyl)-1,3-oxazolidin-2-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13824504N-(cyclohexyl)-N'-(2-chloroethyl)imidazolidinoneYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
195 °C

Procedure

A mixture of cyclohexyl isocyanate (50 mmoles), N-(2-chloroethyl)-2-oxazolidinone (50 mmoles) and anhydrous AlCl3 (40 mg, 0.3 mmole) is heated at 195° C. for 6 hours with stirring. The reaction mixture is dissolved in dichloromethane and the resulting solution is washed with water twice. The dichloromethane solution is dried and evaporated and the residue distilled at reduced pressure. The distillate is recrystallized from hot hexane to give a 50 percent yield of the desired product, m.p. 60° C.-64° C.

Workup

  1. washthe resulting solution is washed with water twice
  2. dry with materialThe dichloromethane solution is dried
  3. customevaporated
  4. distillationthe residue distilled at reduced pressure
  5. customThe distillate is recrystallized from hot hexane

Sources & evidence

ORD record
ord-f87341538a644f02b389ec24f511ea04
Source dataset
uspto-grants-1987_02
Patent number
US04642351

Reaction notes

Loading…