Methanol → 2-(2-Chlorophenyl)-4-(2-fluorophenyl)-5-(4-methylthiophenyl) thiazole

HRID 1378597

반응식

HRID 1378597 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1)Br.[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([NH2:25])=[S:24].CO>C(O)C>[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]1[S:24][C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:25]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 27348242-ChlorothiobenzamideHCID 537994631-(2-Fluorophenyl)-2-(4-methylthiophenyl)-2-bromo ethanone

생성물 1

HCID 539795112-(2-Chlorophenyl)-4-(2-fluorophenyl)-5-(4-methylthiophenyl) thiazole수율 79.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 1-(2-fluorophenyl)-2-(4-methylthiophenyl)-2-bromo-ethanone from Step 3 (1.39 g, 4.1 mmol) and 2-chlorothiobenzamide (0.71 g, 4.1 mmol) in 10 mL of ethanol was heated to reflux for 4.4 hours. The solution was cooled to room temperature and poured into 25 mL of methanol, chilled with an ice bath whereupon crystals of pure product formed which were isolated by filtration and air dried to afford the thiazole (1.34 g, 79%): mp 117°-119° C. 1H NMR (CDCl3) 300 MHz 8.37 (m, 1H), 7.62 (m, 2H), 7.49 (d, J=7.7Hz,1H), 7.32 (m, 7H), 7.22 (d, J=8.5Hz, 2H), 2.51 (s, 3H). Mass spectrum M+ +H=412.

후처리

  1. temperatureto reflux for 4.4 hours
  2. temperaturechilled with an ice bath whereupon crystals of pure product
  3. customformed which
  4. customwere isolated by filtration and air
  5. customdried

출처 및 근거

ORD 기록
ord-b701e2d725d546379db794ba1ebfcbe9
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668161

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