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

HRID 1406292

反応式

HRID 1406292 の反応式
[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]

参加物

5

反応物 2

HCID 67184N-bromobutanimide2 回HCID 567306Ethyl 4-methyl-1,3-thiazole-2-carboxylate

生成物 1

HCID 59338079Ethyl 5-bromo-4-methylthiazole-2-carboxylate収率 50.5%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-85d2022f62b04ebfb72966300909d3ca
出典データセット
uspto-grants-2014_12
特許番号
US08916593B2

関連ノート

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