Cesium carbonate → (1Z)-1-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazinan-2-ylidene]-3-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]ethyl]urea

HRID 924297

反応式

HRID 924297 の反応式
[N:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:13]=2)=[CH:8][CH:7]=1)=[C:2]=[O:3].[CH:28]([C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][C:32]=1[NH:38][C:39]([NH2:41])=[S:40])([CH3:30])[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+].[C:48](Cl)(=[O:51])[CH:49]=[CH2:50]>C(#N)C.C(OCC)(=O)C>[CH:28]([C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][C:32]=1[N:38]1[C:48](=[O:51])[CH2:49][CH2:50][S:40]/[C:39]/1=[N:41]\[C:2]([NH:1][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:26])([F:25])[F:27])=[CH:19][CH:18]=3)[N:13]=2)=[CH:8][CH:7]=1)=[O:3])([CH3:30])[CH3:29]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 13140Acryloyl chlorideHCID 893731681-(2-Isopropyl-5-methylphenyl)thioureaHCID 904044083-(4-(2-Isocyanatoethyl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

生成物 1

HCID 90413005(1Z)-1-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazinan-2-ylidene]-3-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]ethyl]urea収率 44%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

3-(4-(2-Isocyanatoethyl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C34a) (0.18 g, 0.47 mmol), 1-(2-isopropyl-5-methylphenyl)thiourea (0.10 g, 0.50 mmol), and cesium carbonate (0.21 g, 0.63 mmol) in acetonitrile (2.3 mL) were stirred at room temperature overnight. The reaction was diluted with ethyl acetate and washed with water. The organic layers were dried over sodium sulfate, filtered, and concentrated. The crude material was dissolved in butanone (2.3 mL) followed by addition of acryloyl chloride (0.045 mL, 0.55 mmol). The reaction was heated at 40° C. for 4 hours. The reaction was cooled and concentrated. Purification by flash column chromatography using 0-100% ethyl acetate/B, where B=1:1 dichloromethane/hexanes, as eluent followed by drying in a vacuum oven provided the title compound as a yellow oil (0.13 g, 44%).

後処理

  1. washwashed with water
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe crude material was dissolved in butanone (2.3 mL)
  6. temperatureThe reaction was cooled
  7. concentrationconcentrated
  8. customPurification by flash column chromatography
  9. customby drying in a vacuum oven

出典と根拠

ORDレコード
ord-37bc00dd629e4c6b81702d5d2904773f
出典データセット
uspto-grants-2016_03
特許番号
US09278964B2

関連ノート

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