Water → 3',5'-dinitro-N-ethylacetanilide

HRID 1283965

Reaction equation

HRID 1283965 reaction equation
[H-].[Na+].[CH2:3](I)[CH3:4].[N+:6]([C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1)[NH:12][C:13](=[O:15])[CH3:14])([O-:8])=[O:7].O>CN(C)C=O>[N+:6]([C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1)[N:12]([CH2:3][CH3:4])[C:13](=[O:15])[CH3:14])([O-:8])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 181595N-(3,5-dinitrophenyl)acetamide

Product 1

HCID 215171263',5'-dinitro-N-ethylacetanilide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (50% in mineral oil; 1.44 g.), followed by ethyl iodide (3.6 ml.), were added, in small portions during 2 minutes, to a warm stirred solution of 3',5'-dinitroacetanilide (6.75 g.) in dimethylformamide (20 ml.). The mixture was heated on the steam bath for 150 minutes, then cooled, poured into water (400 ml.) and extracted with ethyl acetate (3 × 100 ml.). The combined organic extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was purified by chromatography on alumina (150 g.) using benzene as the eluant. The fractions containing the required product were combined, evaporated to dryness and the residue crystallised from ethanol, to give 3',5'-dinitro-N-ethylacetanilide (4.2 g.), m.p. 126°-127°C.

Workup

  1. additionwere added, in small portions during 2 minutes, to a warm
  2. temperatureThe mixture was heated on the steam bath for 150 minutes
  3. temperaturecooled
  4. extractionextracted with ethyl acetate (3 × 100 ml.)
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated to dryness
  8. customThe residue was purified by chromatography on alumina (150 g.)
  9. additionThe fractions containing the required product
  10. customevaporated to dryness
  11. customthe residue crystallised from ethanol

Sources & evidence

ORD record
ord-ec11cb59f3d248058ae7be7d3aace4e0
Source dataset
uspto-grants-1976_08
Patent number
US03976786

Linked notes

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