Sulfuryl chloride → HCID 20215694, compound

HRID 236514Notes

Reaction equation

HRID 236514 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9].C([Li])CCC.[S:19](Cl)([Cl:22])(=[O:21])=[O:20]>CCOCC>[Cl:1][C:2]1[C:3]([S:8](=[O:9])(=[O:10])[N:11]([CH3:13])[CH3:12])=[C:4]([S:19]([Cl:22])(=[O:21])=[O:20])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 20215695HCID 20215695, compoundHCID 178418339Butyllithium

Product 1

HCID 20215694HCID 20215694, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 29 g of 2-chloro-N,N-dimethylbenzenesulfonamide and 150 mL ether at -5° C. to 0° C. was added dropwise under nitrogen 94 mL of a 1.55M solution of n-butyllithium in hexanes. When the addition was complete, the reaction mixture was allowed to warm to room temperature and was stirred for 2 hours. The reaction mixture was then recooled to -30° C. to -20° C., and treated with a solution of 22 mL of sulfuryl chloride in 60 mL hexanes, added at a rate that maintained the temperature below -10° C. The reaction mixture was then stirred at room temperature for one hour. The precipitated solids were collected, washed with ether and water, and dried to afford 26 g of 3-chloro-2-(N,N-dimethylsulfamoyl)benzenesulfonyl chloride as a yellow solid, which was used without further purification; IR (KBr): 1375, 1350, 1180 and 1160 cm-1.

Workup

  1. additionWhen the addition
  2. customwas then recooled to -30° C. to -20° C.
  3. additionadded at a rate that
  4. temperaturemaintained the temperature below -10° C
  5. stirringThe reaction mixture was then stirred at room temperature for one hour
  6. customThe precipitated solids were collected
  7. washwashed with ether and water
  8. customdried

Sources & evidence

ORD record
ord-0bb60218ca234735a476c5b55ae4c266
Source dataset
uspto-grants-1987_02
Patent number
US04645527

Reaction notes

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