Thioanisole → 2-(3-Tert-butyl-4-hydroxylphenyl)-1-(thiazol-2-yl)ethylamine

HRID 1988275노트

반응식

HRID 1988275 반응식
C(OC([NH:11][CH:12]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=1)=O)C1C=CC=CC=1.C1(SC)C=CC=CC=1.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl.O>[C:21]([C:16]1[CH:15]=[C:14]([CH2:13][CH:12]([NH2:11])[C:25]2[S:26][CH:27]=[CH:28][N:29]=2)[CH:19]=[CH:18][C:17]=1[OH:20])([CH3:24])([CH3:22])[CH3:23]

참가 물질

7

반응물 4

HCID 7520ThioanisoleHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 17819241N-benzyloxycarbonyl-2-(3-tert-butyl-4-hydroxylphenyl)-1-(thiazol-2-yl)ethylamine

생성물 1

HCID 178192062-(3-Tert-butyl-4-hydroxylphenyl)-1-(thiazol-2-yl)ethylamine수율 91.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of N-benzyloxycarbonyl-2-(3-tert-butyl-4-hydroxylphenyl)-1-(thiazol-2-yl)ethylamine (15.28 g, 37.27 mmol) in methylene chloride (1.1 l), thioanisole (8.75 ml, 74.54 mmol) was added. To the mixture, a solution of 1.0M boron tribromide in methylene chloride (186 ml, 186.34 mmol) was added dropwise under cooling with ice and stirred for 1 hour. The reaction mixture was mixed with water and alkalinized by 2N sodium hydroxide and extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure, giving the titled compound (9.46 g, 90%).

후처리

  1. temperatureunder cooling with ice
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-29cc3805e47945599e2cd1e3bc8ce2ee
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553969B1

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