Water → HCID 21517123, compound

HRID 1283962Notes

Reaction equation

HRID 1283962 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[N+:7]([C:10]1[CH:11]=[C:12]([CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=1)[NH2:13])([O-:9])=[O:8].N1C=CC=CC=1.O>CN(C)C=O>[N+:7]([C:10]1[CH:11]=[C:12]([CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=1)[NH:13][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])([O-:9])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 120683,5-DinitroanilineHCID 62325Isobutyryl chloride

Product 1

HCID 21517123HCID 21517123, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

iso-Butyryl chloride (6.3 ml.) was added dropwise during 15 minutes to a stirred solution of 3,5-dinitroaniline (5.5 g.) in a mixture of dimethylformamide (18 ml.) and dry pyridine (18 ml.) maintained at a temperature of 0°-5°C. The reaction mixture was allowed to warm to room temperature during 30 minutes and then added to a mixture of ice and water (200 ml.). The precipitate was filtered off, dissolved in dimethylformamide (50 ml.) and added to a mixture of ice and water (300 ml.) containing concentrated hydrochloric acid (10 ml.). The precipitate was filtered off, washed with saturated aqueous sodium bicarbonate solution and then with water and dried. Crystallisation from aqueous ethanol gave 3',5'-dinitro-iso-butyranilide (5.6 g.), m.p. 165°-168°C.

Workup

  1. temperaturemaintained at a temperature of 0°-5°C
  2. filtrationThe precipitate was filtered off
  3. dissolutiondissolved in dimethylformamide (50 ml.)
  4. additionadded to a mixture of ice and water (300 ml.)
  5. additioncontaining concentrated hydrochloric acid (10 ml.)
  6. filtrationThe precipitate was filtered off
  7. washwashed with saturated aqueous sodium bicarbonate solution
  8. dry with materialwith water and dried
  9. customCrystallisation from aqueous ethanol

Sources & evidence

ORD record
ord-026eb0d144a447b781ecd37cad983e2a
Source dataset
uspto-grants-1976_08
Patent number
US03976786

Reaction notes

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