Water → 4-Chloro-1-(3,5-dimethylisoxazol-4-yl-sulphonyl)-5-(4-tolyl)-imidazole-2-carbonitrile

HRID 1638222Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[N:9]=[C:10]([C:20]#[N:21])[NH:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.[CH3:22][C:23]1[C:27]([S:28](Cl)(=[O:30])=[O:29])=[C:26]([CH3:32])[O:25][N:24]=1.O>C(#N)C>[Cl:7][C:8]1[N:9]=[C:10]([C:20]#[N:21])[N:11]([S:28]([C:27]2[C:23]([CH3:22])=[N:24][O:25][C:26]=2[CH3:32])(=[O:30])=[O:29])[C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 20 °C

Procedure

2.0 g (15 mmol) of potassium carbonate are added to a solution of 2.2 g (10 mmol) of 4-chloro-5-(4-tolyl)-imidazole-2-carbonitrile in 30 ml of acetonitrile, and the mixture is stirred at 20° C. for 10 minutes. The mixture is subsequently admixed with 1.9 g (10 mmol) of 3,5-dimethylisoxazole-4-sulphonyl chloride and stirred at 20° C. for 4 hours. The reaction mixture is then poured into 150 ml of water and extracted with 50 ml of ethyl acetate. The combined organic phases are dried over sodium sulphate and then concentrated under reduced pressure. The residue that remains is chromatographed over silica gel using methylene chloride as mobile phase. Concentration of the eluate under reduced pressure gives 1.8 g (50% of theory) of 4-chloro-1-(3,5-dimethylisoxazol-4-yl-sulphonyl)-5-(4-tolyl)-imidazole-2-carbonitrile in the form of a colourless solid of melting point 103 to 108° C.

Workup

stirringstirred at 20° C. for 4 hours
extractionextracted with 50 ml of ethyl acetate
dry with materialThe combined organic phases are dried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe residue that remains is chromatographed over silica gel

Sources & evidence

ORD record: ord-c80ca4ec130f47c7a186eadd5e0985f6
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043377

Reaction notes

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