Benzamide → 4'-Nitrobenzanilide

HRID 2253859Notes

Reaction equation

HRID 2253859 reaction equation
O.O.[OH-].C[N+](C)(C)C.[C:9]([NH2:17])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N+:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([O-:20])=[O:19]>C1(C)C(C)=CC=CC=1>[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([NH:17][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 2331BenzamideHCID 7416NitrobenzeneHCID 22116808Tetramethylammonium hydroxide dihydrate

Product 1

HCID 769304'-NitrobenzanilideYield 25%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of tetramethylammonium hydroxide dihydrate (TMA(H)·2H2O) (1.8 g, 14.0 mmole), benzamide (1.2 g., 9.9 mmole) and 10 ml of xylene was stirred under nitrogen at 70° C. The water and xylene was removed by vacuum distillation at 740 mmHg/70° C. Nitrobenzene (1.2 g., 9.7 mmole) was added dropwise and the solution was stirred for 4 hours under nitrogen after which time an aliquot was removed for HPLC analysis. 4'-Nitrobenzanilide was produced in 25% yield based on benzamide. Azoxybenzene was generated in 8% yield in this reaction.

Workup

  1. customThe water and xylene was removed by vacuum distillation at 740 mmHg/70° C
  2. customwas removed for HPLC analysis

Sources & evidence

ORD record
ord-d1dfb1fb4990412d9e4c91f1e939bbfd
Source dataset
uspto-grants-1993_08
Patent number
US05233010

Reaction notes

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