4-Nitroaniline → 4,4'-Dinitrocarbanilide

HRID 648073

Reaction equation

HRID 648073 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])OC)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:15]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)([O-:17])=[O:16]>CO>[N+:15]([C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[O:14])=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 74752Carbamic acid, N-(4-nitrophenyl)-, methyl ester

Product 1

HCID 95094,4'-Dinitrocarbanilide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

One proceeds as described in Example 6 with the difference that a distillating column is attached to the flask, the mixture is maintained in gentle boiling and methanol is removed continuously from the mixture. After 2 hours of reaction the end-product is filtered off, 50 mmoles of methyl N-(4-nitrophenyl)-carbamate and 50 mmoles of 4-nitroaniline are added to the filtrate, and the reaction is repeated. The results of four subsequent cycles are summarized in Table 2.

Workup

  1. customis removed continuously from the mixture
  2. customAfter 2 hours of reaction the end-product
  3. filtrationis filtered off
  4. customThe results of four subsequent cycles

Sources & evidence

ORD record
ord-2010c3624bb14b61a2e6aa310c4b7d50
Source dataset
uspto-grants-1983_10
Patent number
US04410697

Linked notes

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