Sodium Hydroxide → 7-(4-Fluoro-phenyl)-4-methoxy-benzooxazol-2-ylamine

HRID 1611949ノート

反応式

HRID 1611949 の反応式
COC(=O)[NH:4][C:5]1[O:6][C:7]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[C:8]=2[N:9]=1.[OH-].[Na+]>O1CCOCC1.C(O)CO>[F:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]2[C:7]3[O:6][C:5]([NH2:4])=[N:9][C:8]=3[C:10]([O:21][CH3:22])=[CH:11][CH:12]=2)=[CH:19][CH:18]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 69288206[7-(4-Fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester

生成物 1

HCID 222522347-(4-Fluoro-phenyl)-4-methoxy-benzooxazol-2-ylamine収率 42%

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 2.80 g (8.85 mmol) [7-(4-fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester in 100 ml dioxane and 30 ml ethylene glycol was added 100 ml of a 5 N aq. sodium hydroxide solution, and the mixture was heated at 100° C. for 16 h. After cooling to room temperature the mixture was poured onto water and extracted three times with ethyl acetate. The combined organic phases were washed with brine, then dried over sodium sulphate and concentrated in vacuo. Trituration in ether afforded 0.95 g (42%) 7-(4-fluoro-phenyl)-4-methoxy-benzooxazol-2-yl-amine as an off-white solid. ES-MS m/e (%): 259 (M+H+, 100).

後処理

  1. temperatureAfter cooling to room temperature the mixture
  2. additionwas poured onto water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-72ab26b5f9094ee893488c82fac68f44
出典データセット
uspto-grants-2006_01
特許番号
US06992083B2

反応ノート

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