Ammonia → HCID 19912246, compound

HRID 1090960Notes

Reaction equation

HRID 1090960 reaction equation
[Cl:1][C:2]1[C:3](SCC2C=CC=CC=2)=[C:4]([CH:8]([F:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.ClCl.[S:21](Cl)(Cl)(=[O:23])=[O:22].[NH3:26]>C(O)(=O)CC.O.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([F:10])[CH3:9])[C:3]=1[S:21]([NH2:26])(=[O:23])=[O:22]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 24526ChlorineHCID 24648Sulfuryl chlorideHCID 19912243HCID 19912243, compound

Product 1

HCID 19912246HCID 19912246, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1032Propionic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.0 g of 3-chloro-2-phenylmethylthio-(1-fluoroethyl)benzene in a mixture of 45 mL of propionic acid and 1.5 mL of water at -10° was added 5.2 mL of liquified chlorine. The reaction was stirred an additional 30 min and then poured into a mixture of ice/water. The aqueous phase was extracted with n-butyl chloride and the combined organic phase was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and concentrated to provide an oil. The crude sulfonyl chloride was dissolved in 100 mL of THF, cooled to -78° and treated with 1.6 mL of liquified anhydrous ammonia. The reaction was allowed to slowly warm to room temperature and stirred overnight. The solids were removed by filtration and then concentration provided the crude sulfonamide. Recrystallization from ethanol/water yielded 2.7 g of the title compound as a white solid, mp 151°-153°.

Workup

  1. extractionThe aqueous phase was extracted with n-butyl chloride
  2. washthe combined organic phase was washed with saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto provide an oil
  6. temperaturecooled to -78°
  7. stirringstirred overnight
  8. customThe solids were removed by filtration
  9. concentrationconcentration
  10. customprovided the crude sulfonamide
  11. customRecrystallization from ethanol/water

Sources & evidence

ORD record
ord-d28a6ff435c54b34b683bfe876817758
Source dataset
uspto-grants-1992_01
Patent number
US05084086

Reaction notes

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