Sulfuryl chloride → 2-(1H-Pyrazol-1-yl)benzenesulfonyl chloride

HRID 1980789Notes

Reaction equation

HRID 1980789 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1.C([Li])CCC.[S:18](Cl)([Cl:21])(=[O:20])=[O:19]>C(OCC)C.CCCCCC>[N:8]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[S:18]([Cl:21])(=[O:20])=[O:19])[CH:12]=[CH:11][CH:10]=[N:9]1

Participants

6

Reactant 3

HCID 24648Sulfuryl chlorideHCID 27954331-(2-Bromophenyl)-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 136727162-(1H-Pyrazol-1-yl)benzenesulfonyl chloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent2×

Procedure

To a solution of 52 g of 1-(2-bromophenyl)pyrazole in 230 ml of diethyl ether under a nitrogen atmosphere and cooled at -70° C. was added dropwise 175 ml of a 1.6M solution of n-butyl lithium in hexane. The suspension was allowed to warm from -70° C. to -25° C. on its own, then a solution of 37 ml of sulfuryl chloride in 69 ml of hexane was added dropwise at -25° to -20° C. After allowing the suspension to warm to room temperature, the suspension was stirred for 5 hours, then filtered to yield 38 g of crude 2-(1H-pyrazol-1-yl)benzenesulfonyl chloride which was contaminated with inorganic salts.

Workup

  1. temperatureto warm from -70° C. to -25° C. on its own
  2. filtrationfiltered

Sources & evidence

ORD record
ord-ce51fddb89424c778ecec7ad6874b060
Source dataset
uspto-grants-1985_04
Patent number
US04511392

Reaction notes

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