Water → 6-(2-Bromoacetyl)-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17345노트

반응식

HRID 17345 반응식
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:21]#[N:22])[C:10]([CH3:20])=[C:11]([C:15]([O:17]CC)=[CH2:16])[C:12]=3[O:13][CH3:14])[N:8]=2)[CH2:3][CH2:2]1.O.[Br:24]N1C(=O)CCC1=O>O1CCCC1>[Br:24][CH2:17][C:15]([C:11]1[C:12]([O:13][CH3:14])=[C:6]2[O:5][C:4]([CH:1]3[CH2:3][CH2:2]3)=[N:8][C:7]2=[C:9]([C:21]#[N:22])[C:10]=1[CH3:20])=[O:16]

참가 물질

5

반응물 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 68586975HCID 68586975, 화합물

생성물 1

HCID 866308376-(2-Bromoacetyl)-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile수율 81.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-Cyclopropyl-6-[1-(ethoxy)ethenyl]-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile (I-84) (2.58 g, 8.46 mmol) was dissolved in tetrahydrofuran (130 ml), water (7.7 ml) and N-bromosuccinimide (1.61 g, 8.89 mmol) were added all at a time, followed by stirring at room temperature for 1.5 hours. After the reaction, the solvent was evaporated away under reduced pressure, followed by dilution with ethyl acetate and by washing with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography (covering) and eluted with a mixed solvent of n-hexane/ethyl acetate (2:1, v/v) to obtain the entitled compound (2.40 g, 81%) as a yellow white solid.

후처리

  1. customAfter the reaction
  2. customthe solvent was evaporated away under reduced pressure
  3. washby washing with water and saturated brine
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated away under reduced pressure
  6. washeluted with a mixed solvent of n-hexane/ethyl acetate (2:1

출처 및 근거

ORD 기록
ord-8c7f0e59410842f6a5c9846b05f992ab
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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