2-Nitro-4-phenylenediamine → 1,4-Bis-(omega-ethoxycarbonyl-acetylamino)-2-nitrobenzene

HRID 1580772Notes

Reaction equation

HRID 1580772 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].[Cl-].[CH2:13]([O:15][C:16](=[O:21])[CH2:17][C:18](O)=[O:19])[CH3:14]>C1C=CC=CC=1>[CH2:13]([O:15][C:16]([CH2:17][C:18]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:18](=[O:19])[CH2:17][C:16]([O:15][CH2:13][CH3:14])=[O:21])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])=[O:19])=[O:21])[CH3:14]

Participants

4

Reactant 2

HCID 43383702-Nitro-4-phenylenediamineHCID 21107838Malonic acid monoethylester chloride

Product 1

HCID 203760821,4-Bis-(omega-ethoxycarbonyl-acetylamino)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

15.3 gm (0.1 mol) of 1,4-diamino-2-nitrobenzene were heated in 160 ml of absolute benzene together with 30.1 gm (0.2 mol) of malonic acid monoethylester chloride for 31/2 hours at refluxing. After cooling the precipitate was suctioned off and recrystallized twice from isopropanol. The product had a melting point of 96°-97°C.

Workup

  1. temperatureat refluxing
  2. temperatureAfter cooling the precipitate
  3. customrecrystallized twice from isopropanol

Sources & evidence

ORD record
ord-fff392482a554ee8bcad22458a5a2ec5
Source dataset
uspto-grants-1976_01
Patent number
US03933886

Reaction notes

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