Methyl iodide → 4-Methoxybenzo[d]oxazol-2-amine

HRID 1611931ノート

反応式

HRID 1611931 の反応式
[NH2:1][C:2]1[O:3][C:4]2[C:5](=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=2)[N:6]=1.[H-].[Na+].I[CH3:15]>O1CCCC1>[CH3:15][O:11][C:7]1[C:5]2[N:6]=[C:2]([NH2:1])[O:3][C:4]=2[CH:10]=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 218650524-Hydroxy-2-aminobenzoxazol

生成物 1

HCID 222522444-Methoxybenzo[d]oxazol-2-amine収率 69.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

To a stirred solution of 10 g (66 mmol) 2-amino-benzooxazol-4-ol in 100 ml tetrahydrofuran at room temperature was added portionwise 3.49 g (79.9 mmol) sodium hydride (55% dispersion in oil), and the mixture was then stirred for 1 h at 50° C. A solution of 14.5 ml (233 mmol) iodomethane in 500 ml tetrahydrofuran was then added dropwise over 3 h, while the reaction mixture was maintained at 50° C. The mixture was then poured onto water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated brine, dried over sodium sulfate, and concentrated in vacuo. Flash chromatography (dichloromethane then 2/98 methanol/dichloromethane) afforded 7.5 g (69%) 4-methoxy-benzooxazol-2-yl-amine as a brown crystalline solid. EI-MS m/e (%): 164 (M+, 100), 149 ([M−CH3]+, 23), 135 (46).

後処理

  1. temperaturewas maintained at 50° C
  2. additionThe mixture was then poured onto water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases were washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-9cc819735c444ffc9635e18473b2f29b
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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