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

HRID 235989

Reaktionsgleichung

Reaktionsgleichung von HRID 235989
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 13824503N-(3-chlorophenyl)-N'-(2-chloroethyl)imidazolidinoneAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6451240Aluminum(III) ChlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
195 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-94979adb2c224e2eab50346924169805
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04642351

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