Pyridine → 2-(4-Chloro-phenyl)-1-(4-methanesulfonyl-phenyl)-1H-imidazole-4-carbonitrile

HRID 1166397Notes

Reaction equation

HRID 1166397 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=3)[CH:10]=[C:11]([CH:13]=O)[N:12]=2)=[CH:4][CH:3]=1.[N:25]1C=CC=CC=1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=3)[CH:10]=[C:11]([C:13]#[N:25])[N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 117929022-(4-Chloro-phenyl)-1-(4-methanesulfonyl-phenyl)-1H-imidazole-4-carbaldehyde

Product 1

HCID 107845892-(4-Chloro-phenyl)-1-(4-methanesulfonyl-phenyl)-1H-imidazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 82 mg (0.23 mmole) of 2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole-4-carboxaldehyde (Example 163) and 51 mg (0.45 mmole) of hydroxylamine O-sulfonic acid in 10 ml of absolute ethanol and 1 ml of pyridine was stirred at reflux overnight. After cooling, the mixture was evaporated, and the residue was taken up in dichloromethane. The solution was washed with aqueous sodium bicarbonate, dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue over silica gel using 50% ethyl acetate in hexane as the eluent gave the title compound, 71 mg, as a pure white crystalline solid: mp (DSC) 205° C. Anal. Calc'd. for C17H12ClN3O2S.¼ H2O (MW 362.32): C, 56.36; H. 3.34; N, 11.60. Found: C, 56.49; H, 3.27; N, 11.45.

Workup

  1. temperatureat reflux overnight
  2. temperatureAfter cooling
  3. customthe mixture was evaporated
  4. washThe solution was washed with aqueous sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-08fab2ea0457403697852e1e40662504
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

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