Methyl chloroformate → 4-Methoxycarbonylamino-2-nitroaniline

HRID 1415651Notes

Reaction equation

HRID 1415651 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[N+:6]([C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[NH2:16])([O-:8])=[O:7].C(=O)(O)[O-].[Na+]>O>[CH3:5][O:4][C:2]([NH:15][C:13]1[CH:12]=[CH:11][C:10]([NH2:16])=[C:9]([N+:6]([O-:8])=[O:7])[CH:14]=1)=[O:3]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 43383702-Nitro-4-phenylenediamine

Product 1

HCID 214830664-Methoxycarbonylamino-2-nitroanilineYield 72.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Methyl chloroformate (34 g) was added dropwise with stirring to a mixture of 2-nitro-p-phenylenediamine (50 g), sodium bicarbonate (44.5 g) and water (700 ml). The temperature was maintained at 5° C. during the addition by means of external cooling. After the addition was complete the mixture was allowed to warm to room temperature and the stirring was continued for two hours. The solid was filtered off and recrystallised from isopropanol to give 4-methoxycarbonylamino-2-nitroaniline (50 g), m.p. 171°-172° C.

Workup

  1. additionAfter the addition
  2. temperatureto warm to room temperature
  3. filtrationThe solid was filtered off
  4. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-c61b86d293b24257b9e60c7e38af5bfc
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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