Sulfuric Acid → N-(3,5-dinitrophenyl)acetamide

HRID 1283967

Reaction equation

HRID 1283967 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH2:7])([O-:3])=[O:2].[C:14](OC(=O)C)(=[O:16])[CH3:15].S(=O)(=O)(O)O>C(OCC)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH:7][C:14](=[O:16])[CH3:15])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 120683,5-Dinitroaniline

Product 1

HCID 181595N-(3,5-dinitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3,5-dinitroaniline (12.8 g.) and acetic anhydride (64 ml.) was stirred during the dropwise addition of concentrated sulphuric acid (1.0 ml.). The temperature of the reaction mixture rose to about 45°C., and afer a few minutes colourless crystals were deposited. Afer 1 hour the reaction mixture was diluted with diethyl ether (200 ml.) and the crystalline solid was filtered off. Recrystallisation from a mixture of ethanol and water (2:1 by volume) gave 3',5'-dinitroacetanilide (11.5 g.) in the form of colourless plates, m.p. 191°-193°C.

Workup

  1. customrose to about 45°C.
  2. customafer a few minutes colourless crystals
  3. filtrationthe crystalline solid was filtered off
  4. customRecrystallisation
  5. additionfrom a mixture of ethanol and water (2:1 by volume)

Sources & evidence

ORD record
ord-a055df0726b748719de0ff4f6b665605
Source dataset
uspto-grants-1976_08
Patent number
US03976786

Linked notes

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