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

HRID 372498Notes

Reaction equation

HRID 372498 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 recrystalized 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 recrystalized from aqueous acetone

Sources & evidence

ORD record
ord-0b53cf2a0aa7400690dd82941b7b3c6a
Source dataset
uspto-grants-1978_05
Patent number
US04091097

Reaction notes

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