N-bromobutanimide → Ethyl 2-(bromomethyl)thiazole-5-carboxylate

HRID 1268892ノート

反応式

HRID 1268892 の反応式
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[S:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:14]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:9][C:10]1[S:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:14]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 12808791Ethyl 2-methyl-1,3-thiazole-5-carboxylate

生成物 1

HCID 21840919Ethyl 2-(bromomethyl)thiazole-5-carboxylate収率 41.7%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

N-Bromosuccinimide (0.91 g, 5.1 mmol) was added to a solution of ethyl 2-methyl-thiazole-5-carboxylate (0.8 g, 4.7 mmol) in carbon tetrachloride. The resultant reaction mixture was stirred for one hour whilist being illuminated by a photoflood lamp. After removing the solvent from the reaction mixture the resultant material was partitioned between ethyl acetate and water. The organic phase was then separated off, dried (MgSO4) and the evaporated. Chromatography on silica, eluting with 30% ethyl acetate in hexane, gave ethyl 2-(bromomethyl)-1,3-thiazole-5-carboxylate (490 mgs), NMR: δH (300 MHz, DMSO-d6, 1.20–1.38 (3 H,t); 4.20–4.37 (2 H,q); 5.05 (2 H, s); 8.55 (1 H, s).

後処理

  1. customThe resultant reaction mixture
  2. customwhilist being illuminated by a photoflood lamp
  3. customAfter removing the solvent from the reaction mixture the resultant material
  4. customwas partitioned between ethyl acetate and water
  5. customThe organic phase was then separated off
  6. dry with materialdried (MgSO4)
  7. washChromatography on silica, eluting with 30% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-4daf22f70f514f42823ad518173ab37b
出典データセット
uspto-grants-2007_04
特許番号
US07199140B2

反応ノート

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