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

HRID 1353010Notes

Reaction equation

HRID 1353010 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.¼H2O (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-1e996805328e49ddad99fb8942a8abe9
Source dataset
uspto-grants-2007_05
Patent number
US07220770B2

Reaction notes

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