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

HRID 437933

반응식

HRID 437933 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 180Acetone용매2회HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

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 acetyl-salicylic 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 1 N 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.

후처리

  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 1 N 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

출처 및 근거

ORD 기록
ord-b1aaf3b3614749d6bd969b2015b3de0c
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04032635

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