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

HRID 372499

反応式

HRID 372499 の反応式
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

参加物

9

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 180Acetone溶媒

反応条件

温度
0 °C

実験手順

Acetylsalicylic 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.

後処理

  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

出典と根拠

ORDレコード
ord-78f9c8f850fa47f8b701f176f07edd1e
出典データセット
uspto-grants-1978_05
特許番号
US04091097

関連ノート

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