Hydrochloric Acid → 2',4-Dihydroxy-3,5-dimethylbenzanilide

HRID 2398278

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HRID 2398278 반응식
C([O:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)C(O)=O)(=O)C.N[C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[C:17]([CH3:23])[CH:16]=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:39](NC1CCCCC1)([NH:41]C1CCCCC1)=[O:40].[OH-].[Na+].Cl>C(O)CO.CC(C)=O>[OH:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[NH:41][C:39](=[O:40])[C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[C:17]([CH3:23])[CH:16]=1

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 2244AspirinHCID 4277N,N'-DicyclohexylureaHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 826684-Amino-2,6-dimethylphenol

생성물 1

HCID 203275582',4-Dihydroxy-3,5-dimethylbenzanilide

시약·촉매·용매 2

HCID 174Ethylene Glycol용매HCID 180Acetone용매

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온도
0 °C

실험 절차

Acetylsalicyclic acid (50 mg.) and 4-amino-2,6-dimethylphenol (38 mg.) were dissolved in ethylene glycol (5 ml.) to which under cooling at 0° C. was added dicyclohexyl carbodiimide (65 mg.). After reaction for several hours the formed dicyclohexylurea was filtered off and the filtrate evaporated to dryness to give a powder which was dissolved in acetone (2 ml.); after adding 2 N sodium hydroxide (4 ml.), the solution was allowed to stand for several hours at room temperature. The addition of 2 N hydrochloric acid (20 ml.) gave a precipitate which was collected by filtration, washed with water and dried at 50° C. under reduced pressure to give solid 2',4-dihydroxy-3,5-dimethylbenzanilide as a powder which was then purified by column chromatography using Sephadex LH-20 resin and elution with methanol. The eluate was evaporated to dryness to give a solid which was recrystallized from aqueous acetone to give white crystals (57.8 mg.) of 2',4-dihydroxy-3,5-dimethylbenzanilide. Yield: 80.9%. Melting point: 142°-145° C.

후처리

  1. filtrationwas filtered off
  2. customthe filtrate evaporated to dryness
  3. customto give a powder which
  4. waitto stand for several hours at room temperature
  5. customgave a precipitate which
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customdried at 50° C. under reduced pressure

출처 및 근거

ORD 기록
ord-9b9a470b46fc4381847be282ed897f77
출처 데이터셋
uspto-grants-1977_05
특허 번호
US04024253

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