Benzenesulfonyl chloride → HCID 20378263, compound

HRID 2051956Notes

Reaction equation

HRID 2051956 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[C:26]1([S:32](Cl)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(COC)OC>[C:26]1([S:32]([N:11]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[N:9]=[CH:10]2)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 10848647HCID 10848647, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20378263HCID 20378263, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a stirred mixture of 10.0 g (0.04 mole) of 4,5-bis(4-fluorophenyl)imidazole and 4.8 g (0.043 mole) of potassium t-butoxide in 150 ml glyme at 0° was added dropwise a solution of 7.6 g (0.043 mole) of benzenesulfonyl chloride in 25 ml glyme. The mixture was stirred at 0° one hour, then at room temperature overnight. The mixture was poured into ice water and the solid was collected and air dried to give 15.2 g, mp 172°-5°. Recrystallization from toluene/methylcyclohexane gave 12.3 g of 1-benzenesulfonyl-4,5-bis(4-fluorophenyl)imidazole as a white solid, mp 181°-2°.

Workup

  1. customat room temperature
  2. customovernight
  3. customthe solid was collected
  4. customair dried
  5. customto give 15.2 g, mp 172°-5°
  6. customRecrystallization from toluene/methylcyclohexane

Sources & evidence

ORD record
ord-c62b64012f91436085eef1fd5dfa778c
Source dataset
uspto-grants-1980_01
Patent number
US04182769

Reaction notes

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