N-bromobutanimide → Ethyl 5-amino-2-bromothiazole-4-carboxylate

HRID 512542노트

반응식

HRID 512542 반응식
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]([C:14]1[N:15]=[CH:16][S:17][C:18]=1[NH2:19])=[O:13])[CH3:10]>C(#N)C.CCOC(C)=O>[NH2:19][C:18]1[S:17][C:16]([Br:1])=[N:15][C:14]=1[C:12]([O:11][CH2:9][CH3:10])=[O:13]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 12620181Ethyl 5-amino-1,3-thiazole-4-carboxylate

생성물 1

HCID 59355801Ethyl 5-amino-2-bromothiazole-4-carboxylate수율 58.2%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

N-Bromosuccinimide (0.54 g, 3.03 mmol) was added to a solution of 5-aminothiazole-4-carboxylic acid ethyl ester (0.44 g, 2.53 mmol) [prepared according to the procedure described by Golankiewicz et al. (Tetrahedron, 41 (24), 5989-5994 (1985))] in acetonitrile (10 mL), and the mixture was stirred for 30 min. The reaction mixture was diluted with EtOAc (50 mL) and washed with 5% K2CO3 aq. solution (25 mL) followed by brine (25mL). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography eluted with 15% EtOAc in hexane to give 0.37 g (58% yield) of the titled compound.

후처리

  1. customprepared
  2. washwashed with 5% K2CO3 aq. solution (25 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted with 15% EtOAc in hexane

출처 및 근거

ORD 기록
ord-939b78f90ce94b139a36b81af49567f9
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102637B2

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