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

HRID 1611931노트

반응식

HRID 1611931 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 222522444-Methoxybenzo[d]oxazol-2-amine수율 69.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9cc819735c444ffc9635e18473b2f29b
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06992083B2

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