Potassium Carbonate → 5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-N-1,3,4-thiadiazol-2-yl-4-{[3-(trifluoromethyl)phenyl]thio}benzenesulfonamide

HRID 509103

Reaktionsgleichung

Reaktionsgleichung von HRID 509103
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[C:20](F)=[CH:21][C:22]([F:45])=[C:23]([S:25]([N:28]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][C:36]=2[O:43][CH3:44])[C:29]2[S:30][CH:31]=[N:32][N:33]=2)(=[O:27])=[O:26])[CH:24]=1>CS(C)=O>[Cl:18][C:19]1[C:20]([S:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=2)=[CH:21][C:22]([F:45])=[C:23]([S:25]([N:28]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][C:36]=2[O:43][CH3:44])[C:29]2[S:30][CH:31]=[N:32][N:33]=2)(=[O:26])=[O:27])[CH:24]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 1367513-(Trifluoromethyl)benzenethiolHCID 580422535-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide

Produkt 1

HCID 666527935-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-N-1,3,4-thiadiazol-2-yl-4-{[3-(trifluoromethyl)phenyl]thio}benzenesulfonamideAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To 3-(trifluoromethyl)thiophenol (0.116 g, 0.649 mmol) in dimethylsulfoxide (5 mL) was added potassium carbonate (0.254 g, 1.62 mmol) followed by 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (Preparation 2, 0.250 g, 0.541 mmol). The reaction mixture was stirred at ambient temperature overnight. The mixture was partitioned between dichloromethane and water and the layers separated by phase separation cartridge. The organic layer was concentrated in vacuo and the resulting residue purified by silica gel flash column chromatography (10%-20% ethyl acetate in heptane gradient elution) to afford the title compound as a solid (0.215 g, 64%).

Aufarbeitung

  1. customThe mixture was partitioned between dichloromethane and water
  2. customthe layers separated by phase separation cartridge
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe resulting residue purified by silica gel flash column chromatography (10%-20% ethyl acetate in heptane gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-5e66a4ac69dd4244b80a5d39a01852a5
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096558B2

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