Dichloromethane → HCID 54412494, 화합물

HRID 1378580노트

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HRID 1378580 반응식
Br[CH:2]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=O.[C:20]([NH2:23])(=[S:22])[CH3:21].C(Cl)Cl.CCCCCC>C(O)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:2]2[S:22][C:20]([CH3:21])=[N:23][C:3]=2[C:5]2[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=2)=[CH:14][CH:15]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 2723949ThioacetamideHCID 54373829HCID 54373829, 화합물

생성물 1

HCID 54412494HCID 54412494, 화합물수율 68%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2-bromo-2-(4-fluorophenyl)-1-(4-methylthiophenyl) ethanone from Step 2 (0.70 g, 2.10 mmol) in ethanol (20 mL) in a 50 mL round bottom flask was added thioacetamide (0.16 g, 2.10 mmol) and the mixture heated to reflux for 20 hours. The reaction was cooled to room temperature and concentrated in vacuo and dissolved in methylene chloride. This solution was washed with NaHCO3 saturated solution and dried over Na2SO4, filtered and reconcentrated in vacuo yielding a white crystalline solid. Flash chromatography of this solid (2:1 methylene chloride: hexane) yielded 5-(4-fluorophenyl)-4-(4-methylthiophenyl) -2-methylthiazole as a white solid (0.45 g, 68%): mp 104°-105° C. 1H NMR (CDCl3) 400 mHz δ7.39 (d, J=8.32, 2H), 7.28 (dd, J=8.80, 5.14, 2H), 7.15 (d, J=8.32, 2H), 7.00 (t, J=8.80, 2H), 2.74 (s, 3H), 2.47 (s, 3H). MS (EI): m/z 316 (M+H). HRMS Δ=0.000 mmu.

후처리

  1. temperaturethe mixture heated
  2. temperatureto reflux for 20 hours
  3. concentrationconcentrated in vacuo
  4. dissolutiondissolved in methylene chloride
  5. washThis solution was washed with NaHCO3 saturated solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customyielding a white crystalline solid

출처 및 근거

ORD 기록
ord-b77f595f1e0f4677a732f530a2e27cf2
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668161

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