Hydrochloric Acid → 3-Cyano-N-1,2,4-thiadiazol-5-yl-4-{[2-(trifluoromethyl)phenyl]thio}benzenesulfonamide

HRID 509096

反応式

HRID 509096 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].C(=O)([O-])[O-].[K+].[K+].[C:18]([C:20]1[CH:21]=[C:22]([S:27]([N:30](CC2C=CC(OC)=CC=2OC)[C:31]2[S:35][N:34]=[CH:33][N:32]=2)(=[O:29])=[O:28])[CH:23]=[CH:24][C:25]=1F)#[N:19].Cl>CN(C)C(=O)C.O1CCOCC1.CS(C)=O>[C:18]([C:20]1[CH:21]=[C:22]([S:27]([NH:30][C:31]2[S:35][N:34]=[CH:33][N:32]=2)(=[O:29])=[O:28])[CH:23]=[CH:24][C:25]=1[S:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:1])([F:10])[F:11])#[N:19]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27778892-(Trifluoromethyl)benzenethiolHCID 580422543-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

生成物 1

HCID 565979253-Cyano-N-1,2,4-thiadiazol-5-yl-4-{[2-(trifluoromethyl)phenyl]thio}benzenesulfonamide

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 312751,4-Dioxane溶媒2 回HCID 31374Dimethylacetamide溶媒

実験手順

2-Trifluoromethylthiophenol (0.0615 g, 0.345 mmol) and potassium carbonate (0.100 g, 0.724 mmol) were stirred in N,N-dimethylacetamide (3 mL). After 5 minutes, 3-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 1, 0.150 g, 0.345 mmol) was added to the reaction mixture and the mixture stirred at ambient temperature overnight. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with a 1M aqueous solution of sodium hydroxide, followed by brine, then dried over MgSO4, filtered and concentrated in vacuo to give a residue. The residue was then dissolved in 1,4-dioxane (1 mL) and a 4M solution of hydrogen chloride in 1,4-dioxane added. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated in vacuo to give a residue. The residue was solubilised in dimethylsulfoxide (1 mL) and purified by the B-HPLC method to afford the title compound.

後処理

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with a 1M aqueous solution of sodium hydroxide
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a residue
  7. stirringThe reaction mixture was stirred at ambient temperature overnight
  8. concentrationThe reaction mixture was concentrated in vacuo
  9. customto give a residue
  10. custompurified by the B-HPLC method

出典と根拠

ORDレコード
ord-34ebe4440f3b46c4afad586b174967af
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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