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Piperidine-1-carbothioamide → 4-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(1-piperidinyl)-thiazole

HRID 1378589
ノート
印刷プレビュー

反応式

HRID 1378589 の反応式
Br[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[N:22]1([C:28](=[S:30])[NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C(O)C.C(Cl)Cl>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:29]=[C:28]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[S:30][C:2]=2[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 1551232Piperidine-1-carbothioamideHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

生成物 1

HCID 229117134-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(1-piperidinyl)-thiazole収率 72%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (0.462 g, 1.24 mmol) (Example 26, Step 2) in ethanol (10 mL) in a 25 mL round bottom flask was added piperidine thiocarboxamide (0.198 g, 1.37 mmol) and the solution was heated to reflux for 14 hours. The reaction was cooled to room temperature and concentrated in vacuo yielding a foam. This foam was dissolved in methylene chloride and washed successively with NaHCO3 saturated solution (3 portions) and brine, dried over Na2SO4, filtered and reconcentrated in vacuo yielding 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(1-piperidinyl)-thiazole (0.371 g, 72%) as a yellow-green fluffy solid: mp 173°-175° C., 1H NMR (CDCl3) 400 mHz δ7.77 (d, J=8.56 Hz, 2H), 7.46 (dd, J=5.60, 8.80), 7.38 (d, J=8.56 Hz, 2H), 6.99 (t, J=8.80 Hz, 2H), 3.53 (s (broad), 4H), 3.05 (s, 3H), 1.70 (s (broad), 6H). MS (EI): m/z 417 (MH+). HRMS Δ=-1.5 mmu.

後処理

  1. temperaturethe solution was heated
  2. temperatureto reflux for 14 hours
  3. concentrationconcentrated in vacuo
  4. customyielding a foam
  5. washwashed successively with NaHCO3 saturated solution (3 portions) and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-738272fce64d454a90d3e308146a8dbc
出典データセット
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05668161

反応ノート

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