N,N-Dimethylaniline → 3,5-Dichloro-2',4-dihydroxy-5'-fluorobenzanilide

HRID 2398277Notes

Reaction equation

HRID 2398277 reaction equation
[F:1][C:2]1[CH:10]=[C:6](C(O)=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:17]=[C:18]([Cl:21])[C:19]=1[OH:20])N.C[N:23]([CH3:30])C1C=CC=CC=1.S(Cl)(Cl)=[O:32]>C1C=CC=CC=1>[Cl:12][C:13]1[CH:14]=[C:15]([CH:17]=[C:18]([Cl:21])[C:19]=1[OH:20])[C:30]([NH:23][C:6]1[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[OH:11])=[O:32]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 24386Thionyl ChlorideHCID 676585-Fluorosalicylic acidHCID 800374-Amino-2,6-dichlorophenol

Product 1

HCID 203275413,5-Dichloro-2',4-dihydroxy-5'-fluorobenzanilideYield 55%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5-Fluorosalicylic acid (5.15 g.) and 3,5-dichloro-4-hydroxyaniline (5.88 g.) were well mixed to which was added benzene (10 ml.) and N,N-dimethylaniline (4.35 ml.). Then with stirring thionyl chloride (3.3 ml.) was added and refluxed 30 minutes. The resulting solution was evaporated and the residue was dissolved in ethyl acetate and subjected to decolorization with activated charcoal followed by washing with 2 N hydrochloric acid and 2.5% sodium bicarbonate solution. The ethyl acetate was then extracted several times with 2 N sodium carbonate solution and the aqueous extracts were combined and brought to pH 1-2 with hydrochloric acid to give a precipitate which was recrystallized from aqueous acetone to give white needle-like crystals (5.7 g.) of 3,5-dichloro-2',4-dihydroxy-5'-fluorobenzanilide. Yield: 55%. Melting point: 227°-229° C.

Workup

  1. temperaturerefluxed 30 minutes
  2. customThe resulting solution was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washby washing with 2 N hydrochloric acid and 2.5% sodium bicarbonate solution
  5. extractionThe ethyl acetate was then extracted several times with 2 N sodium carbonate solution
  6. customto give a precipitate which
  7. customwas recrystallized from aqueous acetone

Sources & evidence

ORD record
ord-66211cfa472d4bd9a1199fbc1b3a3a5b
Source dataset
uspto-grants-1977_05
Patent number
US04024253

Reaction notes

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