Aspirin → HCID 10424739, compound

HRID 437932Notes

Reaction equation

HRID 437932 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[OH:10].C([O:14][C:15]1[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:17](O)=[O:18])(=O)C>CC(C)=O.N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:9])[C:3]=1[OH:10])[NH:8][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=1[OH:14]

Participants

5

Reactant 2

HCID 2244AspirinHCID 800374-Amino-2,6-dichlorophenol

Product 1

HCID 10424739HCID 10424739, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 1049PyridineSolvent

Procedure

2,6-Dichloro-4-aminophenol (0.37 g.) was dissolved in acetone (30 ml.) to which pyridine (0.32 ml.) was added. While mixing, an acetone solution (10 ml.) of the acid chloride prepared from acetylsalicylic acid (0.38 g.) was added by drops. After the reaction was completed, the solution was evaporated under reduced pressure and the residue was dissolved in ethyl acetate and then was washed with water then with 1N-hydrochloric acid. After evaporating off the ethyl acetate under reduced pressure the resulting residue was dissolved in a mixture of methanol and 2N-sodium hydroxide (10 ml. each). The solution was agitated for several hours then acidified with 2N-hydrochloric acid to precipitate the product. By recrystallization in acetone-water, white needle-like crystals of 3',5'-dichloro-2,4'-dihydroxybenzanilide (0.62 g.) were obtained. The yield was 78% and the melting point was 217°-219° C.

Workup

  1. additionwas added
  2. additionWhile mixing
  3. additionwas added by drops
  4. customthe solution was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwas washed with water
  7. customAfter evaporating off the ethyl acetate under reduced pressure the resulting residue
  8. dissolutionwas dissolved in a mixture of methanol and 2N-sodium hydroxide (10 ml
  9. customto precipitate the product
  10. customBy recrystallization in acetone-water

Sources & evidence

ORD record
ord-e367f09be46942a4a662571b37e41e57
Source dataset
uspto-grants-1977_06
Patent number
US04032635

Reaction notes

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