N-bromobutanimide → Ethyl 5-bromo-4-methylthiazole-2-carboxylate

HRID 1406292

반응식

HRID 1406292 반응식
[CH3:1][C:2]1[N:3]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:5][CH:6]=1.C1C(=O)N([Br:19])C(=O)C1>CC#N.CCOC(C)=O>[Br:19][C:6]1[S:5][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:3][C:2]=1[CH3:1]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimide2회HCID 567306Ethyl 4-methyl-1,3-thiazole-2-carboxylate

생성물 1

HCID 59338079Ethyl 5-bromo-4-methylthiazole-2-carboxylate수율 50.5%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

The reaction solution of ethyl 4-methylthiazole-2-carboxylate of preparation 83 (240 mg, 1.40 mmol), NBS (277 mg, 1.14 mmol) in CH3CN (5 mL) was heated at 50° C. for overnight under nitrogen. ˜20% starting material was present by LCMS. Additional portion of NBS (70 mg) was added. The reaction solution was heated at 60° C. for 4 hr, diluted with EtOAc (30 ml), washed with water (2×20 mL), brine, dried over sodium sulfate and purified with a silica gel column by ISCO CombiFlash® chromatography eluting with 0%-20% EtOAc/Heptane to give the title compound as a yellowish oil (177 mg, 50.5%).

후처리

  1. temperatureThe reaction solution was heated at 60° C. for 4 hr
  2. washwashed with water (2×20 mL), brine
  3. dry with materialdried over sodium sulfate
  4. custompurified with a silica gel column by ISCO CombiFlash® chromatography
  5. washeluting with 0%-20% EtOAc/Heptane

출처 및 근거

ORD 기록
ord-85d2022f62b04ebfb72966300909d3ca
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916593B2

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