1,2-Dimethoxyethane → 2-(3-methoxyphenyl)oxazol-4(5H)-one

HRID 643641ノート

反応式

HRID 643641 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH2:8])=[O:7].[H-].[Na+].C[O:15][CH2:16][CH2:17]OC>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[O:7][CH2:17][C:16](=[O:15])[N:8]=2)[CH:9]=[CH:10][CH:11]=1

参加物

4

反応物 3

HCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 984873-Methoxybenzamide

生成物 1

HCID 592629642-(3-methoxyphenyl)oxazol-4(5H)-one収率 26%

反応条件

温度
110 °C

実験手順

2 g (1 eq) of 3-methoxybenzamide was mixed with 3.1 ml (2.7 eq) of chloroacethylchloride and the resulting mixture was heated at 110° C. for 1 h. After cooling, the resulting solid was recrystallized in CHCl3. The resulting solid was added to a suspension of NaH (489 mg, 1.1 eq) in DME at 0° C. After 30 min, the resulting mixture was refluxed for 5 h, cooled to RT and hydrolyzed, extracted with AcOEt, washed with NaCl salt and dried. The resulting solid was recrystallized in a mixture hexane/AcOEt giving 16 as a white solid in 26% yield.

後処理

  1. temperatureAfter cooling
  2. customthe resulting solid was recrystallized in CHCl3
  3. temperaturethe resulting mixture was refluxed for 5 h
  4. temperaturecooled to RT
  5. extractionhydrolyzed, extracted with AcOEt
  6. washwashed with NaCl salt
  7. customdried
  8. customThe resulting solid was recrystallized in a mixture hexane/AcOEt giving 16 as a white solid in 26% yield

出典と根拠

ORDレコード
ord-4cdaffbb45ee4f7db125cd600cab8df6
出典データセット
uspto-grants-2010_04
特許番号
US07700616B2

反応ノート

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