Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate → HCID 58121076、化合物

HRID 1186707ノート

反応式

HRID 1186707 の反応式
[NH2:1][C:2]1[S:3][C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.Br[CH2:19][C:20]([C:22]1[CH:23]=[C+:24][CH:25]=[CH:26][CH:27]=1)=O>C(O)CCC.[Cl-].[Na+].O>[C:7]1([C:5]2[N:6]3[CH:19]=[C:20]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:1]=[C:2]3[S:3][C:4]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

5

反応物 2

HCID 73239Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylateHCID 21362836HCID 21362836、化合物

生成物 1

HCID 58121076HCID 58121076、化合物収率 18.3%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of ethyl 2-amino-4-phenylthiazole-5-carboxylate 93 (0.7 g, 2.82 mmol) and 3-(2-bromoacetyl)benzene-1-ylium 68 (0.34 mL, 2.82 mmol) was stirred at 120° C. in butanol (9 mL) for 3 d. The solution was cooled to room temperature, diluted with brine and extracted with ethyl acetate. The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to afford ethyl 3,6-diphenylimidazo[2,1-b]thiazole-2-carboxylate 94 (0.18 g, 18% yield) as a tan solid after purification by flash chromatography (0 to 30% MeOH in ethyl acetate) followed by trituration in hexane. LRMS (ESI): (calc) 348.42 (found) 349.2 (MH)+

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-8427a942f2804a938f6f43d198cd68ec
出典データセット
uspto-grants-2014_03
特許番号
US08673911B2

反応ノート

読み込み中…