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

HRID 1282937

반응식

HRID 1282937 반응식
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Br:9])[C:3]=1[OH:10].N1C=CC=CC=1.C([O:20][C:21]1[C:22](=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:23](Cl)=[O:24])(=O)C.C(OC1C(=CC=CC=1)C(O)=O)(=O)C>CC(C)=O.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:23](=[O:24])[C:22]1[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=1[OH:20]

참가 물질

7

반응물 4

HCID 1049PyridineHCID 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 2

HCID 180Acetone용매2회HCID 8857Ethyl Acetate용매

실험 절차

2,6-Dibromo-4-aminophenol (0.6 g.) was dissolved in acetone (30 ml.) to which was added pyridine (0.32 ml.). Then dropwise and with stirring the solution was added to an acetone solution (10 ml.) containing acetylsalicyloyl chloride which was prepared from acetylsalicylic acid (0.38 g.). Then the reactant 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 ethyl acetate. The residues were 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 compound melts at 182°-187° C.

후처리

  1. customThen the reactant solution was evaporated to dryness under reduced pressure
  2. customto give a residue which
  3. washAfter washing first with water
  4. customwith 1 N hydrochloric acid, the solution was evaporated under reduced pressure
  5. customto remove ethyl acetate
  6. dissolutionThe residues were redissolved in a mixture of methanol and 2 N sodium hydroxide (10 ml
  7. stirringStirring this solution for several hours
  8. customprecipitated the product which
  9. customwas recrystallized from aqueous methanol

출처 및 근거

ORD 기록
ord-0b46990abb4b4e4cbdd1a612e986ad84
출처 데이터셋
uspto-grants-1976_08
특허 번호
US03973038

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