2-Chloroethanol → 2-Chloroethyl N-(2-chloro-4-nitrophenyl)carbamate

HRID 902998Notes

Reaction equation

HRID 902998 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]=[O:13].[Cl:14][CH2:15][CH2:16][OH:17].CCOCC>CCCCCC>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:13])[O:17][CH2:16][CH2:15][Cl:14]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 3283Diethyl EtherHCID 46142212-Chloro-4-nitrophenyl isocyanate

Product 1

HCID 3107132-Chloroethyl N-(2-chloro-4-nitrophenyl)carbamate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
15 °C

Procedure

50.0 g of 2-chloro-4-nitrophenyl isocyanate was added, with stirring, to 100 g of 2-chloroethanol. After 2 minutes, the temperature of the mixture rose to 65° C. The mixture then was heated at 80°-90° C. for 10 minutes, and cooled. 200 ml of ether and 200 ml of hexane were added, the mixture was cooled to 15° C. and filtered. Drying of the filter cake gave 2-chloroethyl (2-chloro-4-nitrophenyl)carbamate (1A), as a white solid, mp: 128°-130° C.

Workup

  1. customrose to 65° C
  2. temperatureThe mixture then was heated at 80°-90° C. for 10 minutes
  3. temperaturecooled
  4. filtrationfiltered
  5. customDrying of the filter cake

Sources & evidence

ORD record
ord-58878eaa9ab94d928c8cef230751b479
Source dataset
uspto-grants-1980_10
Patent number
US04226612

Reaction notes

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