Water → HCID 15346064, compound

HRID 259742Notes

Reaction equation

HRID 259742 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9](F)=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6].[CH3:16][O:17][C:18]1[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=1.CN(C)C=O.O>O1CCOCC1.C(Cl)Cl.C(OCC)(=O)C>[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([NH:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[O:17][CH3:16])=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6]

Participants

8

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 70002-Methoxyaniline3×HCID 14624893N-(2,5-Difluoro-4-nitrophenyl)acetamide

Product 1

HCID 15346064HCID 15346064, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2',5'-difluoro-4'-nitroacetanilide (20.0 g, 0.093 mol) and o-anisidine (17.1 g, 0.139 mol) in dioxane is refluxed overnight, treated with additional o-anisidine (5.7 g), refluxed for 5 hours, treated with additional o-anisidine (5.7 g), refluxed for 5 days, treated with N,N-dimethylformamide (50 mL), refluxed overnight, cooled to room temperature and poured into water. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a red oil. Flash column chromatography of the oil using silica gel and a 5% ethyl acetate in methylene chloride solution gives the title product as a brown solid which is identified by NMR spectral analyses.

Workup

  1. temperaturerefluxed for 5 hours
  2. temperaturerefluxed for 5 days
  3. temperaturerefluxed overnight
  4. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  5. washwashed sequentially with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a red oil

Sources & evidence

ORD record
ord-d8a2b358130443439ce11040acb27505
Source dataset
uspto-grants-1996_06
Patent number
US05523277

Reaction notes

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