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

HRID 509096

Reaction equation

HRID 509096 reaction equation
[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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-34ebe4440f3b46c4afad586b174967af
Source dataset
uspto-grants-2015_08
Patent number
US09096558B2

Linked notes

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