N,N-Dimethylaniline → HCID 21520611, compound

HRID 1282943Notes

Reaction equation

HRID 1282943 reaction equation
[F:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([OH:20])=[C:15]([Cl:21])[CH:14]=1.CN(C)C1C=CC=CC=1.S(Cl)(Cl)=O>C1C=CC=CC=1>[Cl:19][C:17]1[CH:18]=[C:13]([CH:14]=[C:15]([Cl:21])[C:16]=1[OH:20])[NH:12][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[OH:11]

Participants

6

Reactant 4

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

Product 1

HCID 21520611HCID 21520611, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5Fluorosalicylic acid (5.15 g.) and 4-amino-2,6-dichlorophenol (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-780bb84913894523aad99b4e4b9ded5d
Source dataset
uspto-grants-1976_08
Patent number
US03973038

Reaction notes

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