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

HRID 512542ノート

反応式

HRID 512542 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 59355801Ethyl 5-amino-2-bromothiazole-4-carboxylate収率 58.2%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-939b78f90ce94b139a36b81af49567f9
出典データセット
uspto-grants-2015_08
特許番号
US09102637B2

反応ノート

読み込み中…