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

반응식

HRID 509103 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 666527935-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-N-1,3,4-thiadiazol-2-yl-4-{[3-(trifluoromethyl)phenyl]thio}benzenesulfonamide수율 64.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-5e66a4ac69dd4244b80a5d39a01852a5
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096558B2

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