Isopropyl chloroformate → 4-Isopropoxycarbonylamino-2-nitroaniline

HRID 2071800Notes

Reaction equation

HRID 2071800 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(=O)(O)[O-].[Na+].Cl[C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19]>O>[CH:21]([O:20][C:18]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)=[O:19])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 516892Sodium BicarbonateHCID 43383702-Nitro-4-phenylenediamine

Product 1

HCID 126780374-Isopropoxycarbonylamino-2-nitroanilineYield 96.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred suspension of 2,5-diaminonitrobenzene (60 g.) in a solution of sodium bicarbonate (49.4 g) in water (780 ml) at 10° C. was treated dropwise with isopropyl chloroformate (48 g) and the mixture was stirred at room temperature for 3 hours. The crude brown solid was filtered off, washed well with water and dried to give 4-isopropoxycarbonylamino-2-nitroaniline (90.0 g), m.p. 158°-160° C., which was used in the next stage of the synthesis without further purification being necessary. Recrystallisation of a sample from toluene gave pure 2-nitro-4-isopropoxycarbonylaminoaniline, m.p. 161°-163° C.

Workup

  1. filtrationThe crude brown solid was filtered off
  2. washwashed well with water
  3. customdried

Sources & evidence

ORD record
ord-4719bf74ce124b40ba1dd27f57aaa42a
Source dataset
uspto-grants-1977_09
Patent number
US04048326

Reaction notes

Loading…