Acetic Acid → N,N'-(5-Nitro-1,3-phenylene)diacetamide

HRID 1704704Notes

Reaction equation

HRID 1704704 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[C:6]([NH2:8])[CH:7]=1.C1(C)C=CC=CC=1.[C:19](OC(=O)C)(=[O:21])[CH3:20].[C:26](O)(=[O:28])[CH3:27]>>[C:19]([NH:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[C:6]([NH:8][C:26](=[O:28])[CH3:27])[CH:7]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 7918Acetic AnhydrideHCID 211345-Nitro-1,3-benzenediamine

Product 1

HCID 304565N,N'-(5-Nitro-1,3-phenylene)diacetamide

Procedure

A mixture of 2.5 g. (0.015 mol) of 3,5-diaminonitrobenzene, 100 ml. of toluene, 15 ml. of acetic acid and 3 ml. (3.24 g., 0.32 mol) of acetic anhydride was refluxed for five hours. The reaction mixture was cooled, filtered and the solid washed well with toluene, then boiled in 150 ml. of ethanol for 20 minutes to give 3,5-bis-acetamidonitrobenzene, m.p.>290° C.

Workup

  1. additionA mixture of 2.5 g
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. washthe solid washed well with toluene

Sources & evidence

ORD record
ord-fb02ee80fcde46018c54f3860fd41010
Source dataset
uspto-grants-1978_11
Patent number
US04127646

Reaction notes

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