Triethylamine → 4-(benzyloxy)-N-(2-hydroxy-1,1-dimethylethyl)benzamide

HRID 251436노트

반응식

HRID 251436 반응식
C(Cl)(=O)C(Cl)=O.[CH2:7]([O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[NH2:31][C:32]([CH3:36])([CH3:35])[CH2:33][OH:34]>ClCCl>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:31][C:32]([CH3:36])([CH3:35])[CH2:33][OH:34])=[O:21])=[CH:22][CH:23]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 65578Oxalyl chlorideHCID 738804-(Benzyloxy)benzoic acid

생성물 1

HCID 141804474-(benzyloxy)-N-(2-hydroxy-1,1-dimethylethyl)benzamide수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Oxalyl chloride (6.6 ml, 76 mmol, 1.2 eq) is added into a cold (ice bath) solution of 4-benzyloxy-benzoic acid (14.38 g, 63 mmol, 1 eq) and triethylamine (43.8 ml, 315 mmol, 5 eq) in dichloromethane (400 ml). The dark red mixture is warmed to room temperature and stirred for 2 h and then cooled to 0° C. A solution of 2-amino-2-methyl-propan-1-ol (5.6 g, 63 mmol, 1 eq) in dichloromethane (20 ml) is added and the mixture is stirred overnight at room temperature. The solvent is then removed under vacuum and the residue is dissolved in dichloromethane. This solution is washed once with water and the aqueous layer is extracted with dichloromethane. The organic layers are washed with a solution of 0.1 M sodium hydroxide and dried over magnesium sulfate. The solvent is removed under vacuum, to afford 15 g of 4-(benzyloxy)-N-(2-hydroxy-1,1-dimethylethyl)benzamide ax1 as a brown solid.

후처리

  1. temperaturecooled to 0° C
  2. stirringthe mixture is stirred overnight at room temperature
  3. customThe solvent is then removed under vacuum
  4. dissolutionthe residue is dissolved in dichloromethane
  5. washThis solution is washed once with water
  6. extractionthe aqueous layer is extracted with dichloromethane
  7. washThe organic layers are washed with a solution of 0.1 M sodium hydroxide
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent is removed under vacuum

출처 및 근거

ORD 기록
ord-9863f958e00047f5a0fff65a2349f888
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863450B2

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