Benzenesulfonyl chloride → HCID 20378269, compound

HRID 2051953Notes

Reaction equation

HRID 2051953 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18][C:19]([F:24])([F:23])[CH:20]([F:22])[F:21])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[C:31]1([S:37](Cl)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(COC)OC>[C:31]1([S:37]([N:10]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[C:9]2[S:18][C:19]([F:23])([F:24])[CH:20]([F:22])[F:21])(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 135080754,5-Diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 20378269HCID 20378269, compoundYield 125.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a stirred solution of 7.0 g (0.02 mole) of 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole in 50 ml glyme at 0° was added 3.4 g (0.03 mole) of potassium t-butoxide. The mixture was stirred at 0° for five minutes, then a solution of 5.3 g (0.03 mole) of benzenesulfonyl chloride in 50 ml glyme was added dropwise. The mixture was stirred at 0° for one hour, then at room temperature overnight. The mixture was poured onto ice water and the crude solid product was collected and washed with water and hexane to give 12.4 g of tan solid. The product was purified by chromatography on silica gel, eluting with toluene, to give 7.2 g, white crystals, mp 171.5°-172.5° (from methylcyclohexane).

Workup

  1. stirringThe mixture was stirred at 0° for one hour
  2. customat room temperature
  3. customovernight
  4. additionThe mixture was poured onto ice water
  5. customthe crude solid product was collected
  6. washwashed with water and hexane

Sources & evidence

ORD record
ord-b0d8fd9111c9447fb1d266f7c1e1ac53
Source dataset
uspto-grants-1980_01
Patent number
US04182769

Reaction notes

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