Hydrochloric Acid → 3-cyano-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

HRID 2283653Notes

Reaction equation

HRID 2283653 reaction equation
[OH-].[Na+].[S:3]1[C:7]([NH2:8])=[N:6][CH:5]=[N:4]1.[C:9]([C:11]1[CH:12]=[C:13]([S:18](Cl)(=[O:20])=[O:19])[CH:14]=[CH:15][C:16]=1[F:17])#[N:10].Cl>O.O1CCOCC1>[C:9]([C:11]1[CH:12]=[C:13]([S:18]([NH:8][C:7]2[S:3][N:4]=[CH:5][N:6]=2)(=[O:20])=[O:19])[CH:14]=[CH:15][C:16]=1[F:17])#[N:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2902745-Amino-1,2,4-thiadiazoleHCID 27789083-Cyano-4-fluorobenzenesulfonyl chloride

Product 1

HCID 580423023-cyano-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideYield 120.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Sodium hydroxide (5.08 g, 130 mmol) was dissolved in water (60 mL) and 1,4-dioxane (300 mL). 1,2,4-Thiadiazol-5-amine (10 g, 100 mmol) was added and the reaction mixture was stirred for 5 minutes. 3-Cyano-4-fluorobenzene-1-sulfonyl chloride (8.25 g, 38 mmol) was added and the reaction mixture was allowed to stir for 3 hours at 20° C. After this time, the reaction mixture was poured into 1N aqueous hydrogen chloride solution (150 mL). This solution was extracted with ethyl acetate (3×50 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a brown solid (13 g, 69%).

Workup

  1. stirringto stir for 3 hours at 20° C
  2. extractionThis solution was extracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50cdb67317624a22aa3ac3adf1faa4c6
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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