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

反応式

HRID 509103 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-5e66a4ac69dd4244b80a5d39a01852a5
出典データセット
uspto-grants-2015_08
特許番号
US09096558B2

関連ノート

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