2-Nitroaniline → Carbamic acid, (2-nitrophenyl)-, 2-chloroethyl ester

HRID 1721163Notes

Reaction equation

HRID 1721163 reaction equation
C(=O)([O-])[O-].[Ca+2].[N+:6]([C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH2:11])([O-:8])=[O:7].Cl[C:17]([O:19][CH2:20][CH2:21][Cl:22])=[O:18]>COCCOC.O>[N+:6]([C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH:11][C:17](=[O:18])[O:19][CH2:20][CH2:21][Cl:22])([O-:8])=[O:7]

Participants

6

Reactant 3

HCID 69462-NitroanilineHCID 10112Calcium CarbonateHCID 123052-Chloroethyl chloroformate

Product 1

HCID 22417492Carbamic acid, (2-nitrophenyl)-, 2-chloroethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
78 °C

Procedure

135 g of calcium carbonate are added to a solution of 345.3 g of 2-nitroaniline in a mixture of 1020 g of monoethylene glycol dimethyl ether and 150 g of water and the mixture is heated to 78° C. 375 g of 2-chloroethyl chloroformate are then added in the course of 3 hours. The mixture is subsequently stirred at the reflux temperature for 1.5 hours, until the reaction is complete, and is cooled to 35° C., and the product is precipitated with water and ice. The product is filtered off, washed with water and dried.

Workup

  1. temperatureis cooled to 35° C.
  2. customthe product is precipitated with water and ice
  3. filtrationThe product is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-cf34f7029b1742babf76491caf8933e9
Source dataset
uspto-grants-1996_04
Patent number
US05508467

Reaction notes

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