Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate → HCID 58121076, 화합물

HRID 1186707노트

반응식

HRID 1186707 반응식
[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

참가 물질

5

반응물 2

HCID 73239Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylateHCID 21362836HCID 21362836, 화합물

생성물 1

HCID 58121076HCID 58121076, 화합물수율 18.3%

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 57417360Sodium chloride; water용매

실험 절차

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)+

후처리

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

출처 및 근거

ORD 기록
ord-8427a942f2804a938f6f43d198cd68ec
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673911B2

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