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

HRID 1268892노트

반응식

HRID 1268892 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4daf22f70f514f42823ad518173ab37b
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199140B2

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