Benzene, 1-chloro-3-isocyanato- → N-(3-chlorophenyl)-N'-(2-chloroethyl)imidazolidinone

HRID 235989

Reaction equation

HRID 235989 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:11][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17]OC1=O>ClCCl.[Al+3].[Cl-].[Cl-].[Cl-]>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:17][CH2:18][N:14]([CH2:13][CH2:12][Cl:11])[C:9]2=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 756333-(2-Chloroethyl)-1,3-oxazolidin-2-one

Product 1

HCID 13824503N-(3-chlorophenyl)-N'-(2-chloroethyl)imidazolidinoneYield 78.7%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
195 °C

Procedure

A mixture of 3-chlorophenyl isocyanate (7.65 g, 50 mmoles), N-(2-chloroethyl)-2-oxazolidinone (7.5 g, 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 10.2 g (78.4 percent) of the desired product, m.p. 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-94979adb2c224e2eab50346924169805
Source dataset
uspto-grants-1987_02
Patent number
US04642351

Linked notes

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