Hydrochloric Acid → 3',5'-Dichloro-2-hydroxy-4'-methoxybenzanilide

HRID 1282941Notes

Reaction equation

HRID 1282941 reaction equation
C([O:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:7]([OH:9])=O)(=O)C.S(Cl)(Cl)=O.[NH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[C:22]([O:26][CH3:27])=[C:21]([Cl:28])[CH:20]=1.CN(C)C1C=CC=CC=1.C(OC1C(=CC=CC=1)C(Cl)=O)(=O)C.Cl>CC(C)=O>[Cl:25][C:23]1[CH:24]=[C:19]([CH:20]=[C:21]([Cl:28])[C:22]=1[O:26][CH3:27])[NH:18][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=1[OH:4]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 2244AspirinHCID 24386Thionyl ChlorideHCID 796682-Acetoxybenzoyl chlorideHCID 131786513,5-Dichloro-4-methoxyaniline

Product 1

HCID 215206193',5'-Dichloro-2-hydroxy-4'-methoxybenzanilideYield 64.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

Acetylsalicylic acid (1.8 g.) was converted to its acid chloride by conventional method using thionyl chloride and dissolved in acetone (30 ml.). 4-Amino-2,6-dichloroanisole (2.13 g.) with N,N-dimethylaniline (1.27 ml.) was dissolved in acetone (25 ml.) to which, with stirring in the cold at 0°-10° C., the above acetone solution of acetylsalicyloyl chloride was added dropwise over 20-30 minutes. Reaction continued for 1-2 hours, then the solution was evaporated to dryness under reduced pressure, the residue being put in sodium hydroxide solution and gently agitated for 1-2 hours for cleavage of the acetyl group. After reaction was complete the solution was made acidic by the addition of 2 N hydrochloric acid and the precipitate which formed was collected by filtration and recrystallized from aqueous acetone to give needle-like crystals (2.0 g.) of 3',5'-dichloro-2-hydroxy-4'-methoxybenzanilide. Yield 64%. The melting point of the product is 226°- 228° C.

Workup

  1. customReaction
  2. customthe solution was evaporated to dryness under reduced pressure
  3. stirringgently agitated for 1-2 hours for cleavage of the acetyl group
  4. customAfter reaction
  5. customthe precipitate which formed
  6. filtrationwas collected by filtration
  7. customrecrystallized from aqueous acetone

Sources & evidence

ORD record
ord-e068fb7d97144d31b812f28518a13c41
Source dataset
uspto-grants-1976_08
Patent number
US03973038

Reaction notes

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