2,2,4-Trimethylpentane → 4-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(3,5-dichlorophenylamino)thiazole

HRID 1378615ノート

反応式

HRID 1378615 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.[Cl:22][C:23]1[CH:24]=[C:25]([NH:30][C:31]([NH2:33])=[S:32])[CH:26]=[C:27]([Cl:29])[CH:28]=1.C(CC(C)(C)C)(C)C>C(O)C.C(OCC)(=O)C.C(Cl)Cl>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:33]=[C:31]([NH:30][C:25]3[CH:24]=[C:23]([Cl:22])[CH:28]=[C:27]([Cl:29])[CH:26]=3)[S:32][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

6

反応物 3

HCID 109072,2,4-TrimethylpentaneHCID 27375393,5-DichlorophenylthioureaHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

生成物 1

HCID 229121444-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(3,5-dichlorophenylamino)thiazole収率 63%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (Example 26, Step 2) (0.312, 0.841 mmol) in ethanol (10 mL) in a 25 mL round bottom flask was added N-(3,5-dichlorophenyl)thiourea (0.195 g, 0.882 mmol). The solution was heated to reflux (14 hours) and the reaction was cooled to room temperature. The resulting suspension was concentrated in vacuo, suspended in ethyl acetate (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 powdery solid. This solid was dissolved in ethyl acetate/methylene chloride. Addition of isooctane resulted in the precipitation of 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(3,5-dichlorophenylamino)thiazole (0.261 g, 63%) as a pale yellow powder: mp 287°-288° C.; 1HNMR (DMSO d6) 400 mHz 10.84 (s, 1 H), 7.86 (d, J=8.79 Hz, 2 H), 7.73 (s, 2 H), 7.54-7.45 (m, 4 H), 7.22 (t, J=8.79 Hz, 2 H), 7.15 (s, 1 H), 3.22 (s, 3 H); MS m/z 492 (M+). HRMS Δ=4.8 mmu.

後処理

  1. temperatureThe solution was heated
  2. temperatureto reflux (14 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 powdery solid

出典と根拠

ORDレコード
ord-8d8550e06b2948dca937c246d6f1e992
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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