Pyridine → Ethyl 2-benzamido-4-methylthiazole-5-carboxylate

HRID 45405

반응식

HRID 45405 반응식
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.N1C=CC=CC=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[C:19]([NH:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

생성물 1

HCID 683991Ethyl 2-benzamido-4-methylthiazole-5-carboxylate수율 97%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of ethyl 2-amino-4-methylthiazole-5-carboxylate (2.00 g, 10.00 mmol) in anhydrous dichloromethane (40 mL) was added pyridine (2.50 g, 32.00 mmol), followed by the addition of benzoyl chloride (1.90 g, 13.00 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 18 h, then washed sequentially with 1 N hydrochloric acid (15 mL), saturated aqueous sodium bicarbonate (2×15 mL), and water (15 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a white solid in 97% yield (3.0 g); 1H NMR (CDCl3, 300 MHz) δ 11.35 (s, br, 1H), 7.89 (d, J=7.4 Hz, 2H), 7.59 (t, J=7.4 Hz, 1H), 7.47 (t, J=7.6 Hz, 2H), 4.29 (q, J=7.1 Hz, 2H), 2.28 (s, 3H), 1.35 (t, J=7.1 Hz, 3H); MS (ES+) m/z 291.1 (M+1).

후처리

  1. washwashed sequentially with 1 N hydrochloric acid (15 mL), saturated aqueous sodium bicarbonate (2×15 mL), and water (15 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-a688f488a9d64955b03427bc47f03263
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541457B2

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