Acetic Anhydride → HCID 21517129, compound

HRID 1283964Notes

Reaction equation

HRID 1283964 reaction equation
[CH2:1]([NH:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]([N+:15]([O-:17])=[O:16])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[C:18](OC(=O)C)(=[O:20])[CH3:19]>S(=O)(=O)(O)O>[N+:12]([C:10]1[CH:11]=[C:6]([CH:7]=[C:8]([N+:15]([O-:17])=[O:16])[CH:9]=1)[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:18](=[O:20])[CH3:19])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54053757HCID 54053757, compound

Product 1

HCID 21517129HCID 21517129, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A stirred suspension of N-n-butyl-3,5-dinitroaniline (5.5 g.) in acetic anhydride (20 ml.) was treated with a few drops of concentrated sulphuric acid and then heated on the steam bath for 3 hours. The cooled reaction mixture was added to ice-water (400 ml.) and the product was extracted with ethyl acetate (3 × 100 ml.). The combined organic extract was washed with 2N aqueous sodium bicarbonate solution, dried with anhydrous magnesium sulphate, and the solvent removed in vacuo, to give 3',5'-dinitro-N-n-butylacetanilide (2.8 g.), in the form of an amber syrup, ν1670 cm-1.

Workup

  1. temperatureheated on the steam bath for 3 hours
  2. customThe cooled reaction mixture
  3. extractionthe product was extracted with ethyl acetate (3 × 100 ml.)
  4. extractionThe combined organic extract
  5. washwas washed with 2N aqueous sodium bicarbonate solution
  6. dry with materialdried with anhydrous magnesium sulphate
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-23f4df9701ad4753afa7ba7ed3d1fcea
Source dataset
uspto-grants-1976_08
Patent number
US03976786

Reaction notes

Loading…