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

HRID 1988275ノート

反応式

HRID 1988275 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-29cc3805e47945599e2cd1e3bc8ce2ee
出典データセット
uspto-grants-2009_06
特許番号
US07553969B1

反応ノート

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