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

HRID 251436ノート

反応式

HRID 251436 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9863f958e00047f5a0fff65a2349f888
出典データセット
uspto-grants-2011_01
特許番号
US07863450B2

反応ノート

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