(4-Cyanophenyl)thiourea → HCID 22911871、化合物

HRID 1378616ノート

反応式

HRID 1378616 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.[C:22]([C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH2:33])=[S:32])=[CH:26][CH:25]=1)#[N:23]>C(O)C>[C:22]([C:24]1[CH:25]=[CH:26][C:27]([NH:30][C:31]2[S:32][C:2]([C:12]3[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=3)=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=3)[N:33]=2)=[CH:28][CH:29]=1)#[N:23]

参加物

4

反応物 2

HCID 2757973(4-Cyanophenyl)thioureaHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

生成物 1

HCID 22911871HCID 22911871、化合物収率 53.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (Example 26, Step 2) (0.413, 1.11 mmol) in ethanol (10 mL) in a 25 mL round bottom flask was added N-(4-cyanophenyl)thiourea (0.207 g, 1.17 mmol). The solution was heated to reflux (24 hours) and the reaction was cooled to room temperature. The resulting suspension was concentrated in vacuo, suspended in methylene chloride (100 mL) and washed with sodium carbonate solution (10%, 3×20 mL), brine (1×20 mL), dried over sodium sulfate, filtered and concentrated yielding a solid. This solid was flash chromatographed (1:1, hexane:ethyl acetate with 1% acetic acid). The resulting product was recrystallized from methylene chloride and isooctane yielding 2-(4-cyanophenylamino)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)thiazole (0.266 g, 53%) as a pale yellow solid: mp 273°-274° C.; 1HNMR (DMSO d6) 400 mHz 10.98 (s, 1 H), 7.86 (d, J=8.32 Hz, 2 H), 7.83 (d, J=9.05 Hz, 2 H), 7.76 (d, J=8.80 Hz, 2 H), 7.55-7.47 (m, 4 H), 7.21 (t, J=8.80 Hz, 2 H), 3.22 (s, 3 H); MS m/z 450 (M+H). HRMS Δ=2.6 mmu.

後処理

  1. temperatureThe solution was heated
  2. temperatureto reflux (24 hours)
  3. concentrationThe resulting suspension was concentrated in vacuo
  4. washwashed with sodium carbonate solution (10%, 3×20 mL), brine (1×20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customyielding a solid
  9. customchromatographed (1:1, hexane:ethyl acetate with 1% acetic acid)
  10. customThe resulting product was recrystallized from methylene chloride and isooctane

出典と根拠

ORDレコード
ord-baa7ab97b3074ef7a721894855400b83
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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