1,2-Dibromopropane → (1Z)-1-[3-(2-ethyl-5-methylphenyl)-4-methyl-1,3-thiazolidin-2-ylidene]-3-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]ethyl]urea

HRID 1772523

Reaktionsgleichung

Reaktionsgleichung von HRID 1772523
[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].[CH2:28]([C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][C:31]=1[NH:37][C:38]([NH2:40])=[S:39])[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+].Br[CH2:54][CH:55](Br)[CH3:56]>C(#N)C.CC(=O)CC.O>[CH2:28]([C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][C:31]=1[N:37]1[CH:55]([CH3:56])[CH2:54][S:39]/[C:38]/1=[N:40]\[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])[CH3:29]

Komponenten

9

Edukt 5

HCID 65531,2-DibromopropaneHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 904044083-(4-(2-Isocyanatoethyl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazoleHCID 904045601-(2-Ethyl-5-methylphenyl)thiourea

Produkt 1

HCID 90412375(1Z)-1-[3-(2-ethyl-5-methylphenyl)-4-methyl-1,3-thiazolidin-2-ylidene]-3-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]ethyl]ureaAusbeute 13,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

3-(4-(2-Isocyanatoethyl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C34a)(0.16 g, 0.42 mmol), 1-(2-ethyl-5-methylphenyl)thiourea (CA41) (0.081 g, 0.42 mmol), and cesium carbonate (0.13 g, 0.39 mmol) in acetonitrile (1.9 mL) was stirred at room temperature for 3 hours. The reaction was diluted with butanone (2 mL) and potassium carbonate (0.12 g, 0.83 mmol) and 1,2-dibromopropane (0.090 mL, 0.83 mmol) were added. The reaction was heated to 60° C. for 6 hours. The reaction was diluted with water and extracted with dichloromethane (2×) and the organic layers were filtered through a phase separator and concentrated. Purification by flash column chromatography using 0-100% ethyl acetate/B, where B=1:1 dichloromethane/hexanes, as eluent provided the title compound as a yellow oil (0.034 g, 13%).

Aufarbeitung

  1. additionwere added
  2. extractionextracted with dichloromethane (2×)
  3. filtrationthe organic layers were filtered through a phase separator
  4. concentrationconcentrated
  5. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e7be9f7117794343a8c1d051554eaa8e
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249133B2

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