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

HRID 1378575노트

반응식

HRID 1378575 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)Br)=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([NH2:25])=[S:24]>C(#N)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:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:25]=1

참가 물질

4

반응물 2

HCID 27348242-ChlorothiobenzamideHCID 541605321-(4-Fluorophenyl)-2-(4-methylthiophenyl)-2-bromoethanone

생성물 1

HCID 537877762-(2-Chlorophenyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole수율 50%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylthiophenyl)ethanone (2.03 g, 5.98 mmol) (Example 1, Step 3) in acetonitrile (60mL) in a 125 mL round bottom flask was added 2-chlorothiobenzamide (1.08 g, 6.28 mmol) and the suspension heated to 80° C. for 4 hours. The reaction was cooled to room temperature and the suspension filtered through a fritted funnel. The solid was recrystallized from hot acetonitrile (50 mL) and methanol (150 mL) yielding 2-(2-chlorophenyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole as a tan solid (1.23 g, 50 %): mp 133°-134° C. 1H NMR (CDCl3) 300 mHz δ8.37 (d, J=6.17 Hz, 1H), 7.60 (dd, J=8.68, 5.28, 2H) 7.51 (d, J=9.44 Hz, 1H), 7.32-7.42 (m, 2H), 7.32 (d, J=8.68 Hz, 2H), 7.21 (d, J=8.68 Hz, 2H), 7.02 (t, J=8.68, 2H), 2.51 (s, 3H). MS (EI): m/z 412 (MH+).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe suspension filtered through a fritted funnel
  3. customThe solid was recrystallized from hot acetonitrile (50 mL) and methanol (150 mL)

출처 및 근거

ORD 기록
ord-f6557a6a6e2e4a6a94099d9b9b744e54
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668161

반응 노트

불러오는 중…