2-(Chloromethyl)-2-methyloxirane → N-{2-[(2-Methyl-2-oxiranyl)methoxy]phenyl}benzamide

HRID 490320ノート

反応式

HRID 490320 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl[CH2:18][C:19]1([CH3:22])[CH2:21][O:20]1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH3:18][C:19]1([CH2:22][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:21][O:20]1

参加物

5

反応物 2

HCID 952202-(Chloromethyl)-2-methyloxiraneHCID 231766N-(2-Hydroxyphenyl)benzamide

生成物 1

HCID 85800461N-{2-[(2-Methyl-2-oxiranyl)methoxy]phenyl}benzamide収率 62%

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 962Water溶媒

反応条件

温度
72.5 °C

実験手順

A mixture of N-(2-hydroxyphenyl)benzamide (159 mg; 0.75 mmol), 2-(chloromethyl)-2-methyloxirane (1.60 g, 15 mmol), and benzyltriethylammonium chloride (27 mg, 0.12 mmol) was stirred at 70-75° C. for 6 h After cooling to room temperature, water (2 ml) was added and the mixture was vigorously shaken. It was extracted with dichloromethane (2×5 ml), and the combined organic extracts were washed with aq. NaOH (2M, 5 ml) and water (10 ml). Drying with Na2SO4, evaporation of the solvent and flash chromatography on silica gel with n-heptane/ethyl acetate (ethyl acetate from 25 to 50%) afforded title compound as yellowish solid (131 mg, 0.46 mmol, 62%).

後処理

  1. temperatureAfter cooling to room temperature
  2. stirringthe mixture was vigorously shaken
  3. extractionIt was extracted with dichloromethane (2×5 ml)
  4. washthe combined organic extracts were washed with aq. NaOH (2M, 5 ml) and water (10 ml)
  5. dry with materialDrying with Na2SO4, evaporation of the solvent and flash chromatography on silica gel with n-heptane/ethyl acetate (ethyl acetate from 25 to 50%)

出典と根拠

ORDレコード
ord-01f20dd210404f21ad8a5be1ea66f589
出典データセット
uspto-grants-2009_05
特許番号
US07528156B2

反応ノート

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