Dichloromethane → HCID 54412494、化合物

HRID 1378580ノート

反応式

HRID 1378580 の反応式
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

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 2723949ThioacetamideHCID 54373829HCID 54373829、化合物

生成物 1

HCID 54412494HCID 54412494、化合物収率 68%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b77f595f1e0f4677a732f530a2e27cf2
出典データセット
uspto-grants-1997_09
特許番号
US05668161

反応ノート

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