Chloroacetone → 3-(4-Methyl-1,3-thiazol-2-yl)pyridine

HRID 1913350노트

반응식

HRID 1913350 반응식
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.Cl[CH2:11][C:12](=O)[CH3:13]>C(O)C>[CH3:13][C:12]1[N:9]=[C:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[S:8][CH:11]=1

참가 물질

4

반응물 2

HCID 6571ChloroacetoneHCID 737155Thionicotinamide

생성물 1

HCID 12015543-(4-Methyl-1,3-thiazol-2-yl)pyridine수율 13%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

(See FIG. 10.) To a solution/slurry of thionicotinamide (3.3 g, 23.9 mmol) in ethanol (100 mL) is added chloroacetone (2.28 mL, 28.7 mmol) and the resultant slurry is heated to reflux and stirred for 48 h. The solvent was removed in vacuo and the crude material was chromatographed on silica gel (EtOAc/Hex, 50/50, Rf=0.34) to afford the title compound 26 (543 mg, 13% yield) as a brown solid: mp=42-43° C.; 1H NMR (CDCl3) δ 9.09 (m, 1H), 8.57 (m, 1H), 8.15 (m, 1H), 7.31 (m, 1H), 6.89 (m, 1H), 2.47 (s, 3E1); LRMS (ESI) calcd for C9H8N2S [M+H]+ 177. found 177.

후처리

  1. temperaturethe resultant slurry is heated
  2. temperatureto reflux
  3. customThe solvent was removed in vacuo
  4. customthe crude material was chromatographed on silica gel (EtOAc/Hex, 50/50, Rf=0.34)

출처 및 근거

ORD 기록
ord-db3c8c63af0d4b1f8ce0beea1c7a0e6c
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609708B2

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