Aspirin → Benzamide, N-(3,5-dibromo-4-hydroxyphenyl)-2-hydroxy-

HRID 616192

Reaction equation

HRID 616192 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Br: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](Cl)=[O:18])(=O)C.C(OC1C(=CC=CC=1)C(O)=O)(=O)C>CC(C)=O.N1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Br: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

7

Reactant 3

HCID 2244AspirinHCID 691074-Amino-2,6-dibromophenolHCID 796682-Acetoxybenzoyl chloride

Product 1

HCID 3043338Benzamide, N-(3,5-dibromo-4-hydroxyphenyl)-2-hydroxy-Yield 78%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,6-Dibromo-4-aminophenol (0.6 g.) was dissolved in acetone (30 ml.) to which pyridine (0.32 ml.) was added. Then the solution was added by drops and with stirring to an acetone solution (10 ml.) containing acetylsalicyloyl chloride which was prepared from acetylsalicylic acid (0.38 g.). The resulting solution was evaporated to dryness under reduced pressure to give a residue which was dissolved in ethyl acetate. After washing first with water and then with 1N hydrochloric acid the solution was evaporated under reduced pressure to remove the ethyl acetate. The residue was redissolved in a mixture of methanol and 2 N sodium hydroxide (10 ml. each). Stirring this solution for several hours and acidifying with 2 N hydrochloric acid precipitated the product which was recrystallized from aqueous methanol to give light brown crystals of 3',5'-dibromo-2,4'-dihydroxybenzanilide (0.88 g.). Yield: 78%. The melting point of the compound is 182°-187° C.

Workup

  1. additionwas added
  2. additionThen the solution was added by drops
  3. customThe resulting solution was evaporated to dryness under reduced pressure
  4. customto give a residue which
  5. washAfter washing first with water
  6. customwith 1N hydrochloric acid the solution was evaporated under reduced pressure
  7. customto remove the ethyl acetate
  8. dissolutionThe residue was redissolved in a mixture of methanol and 2 N sodium hydroxide (10 ml
  9. customprecipitated the product which
  10. customwas recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-5fca433ef1414882b947dee9475eb87c
Source dataset
uspto-grants-1978_02
Patent number
US04072753

Linked notes

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