4-(ISOPROPYLSULFONYL)-1H-IMIDAZOLE synthesis

Yield:-

Reaction Conditions:

Stage #1:4-(isopropylthio)-1H-imidazole with 3-chloro-benzenecarboperoxoic acid;trifluoroacetic acid in dichloromethane at 0 - 20;
Stage #2: with sodium hydroxide in dichloromethane;water

Steps:

To a stirred solution of 1.00 g (l-6a) in dichloromethane (14 ml_) at 0⁰C was added trifluoroacetic acid (0.54 ml_) followed by m-chloroperbenzoic acid (6.07 g) was added in portions. An additional 10 ml_ dichloromethane was added to the mixture and stirring continued. After 20 minutes, the ice bath was removed and the reaction stirred at room temperature for another 30 minutes before adding 1 equivalent of 1 N NaOH (7.03 ml_). The mixture was concentrated and the residue purified by flash column chromatography (SiO₂, ethyl acetate/heptane 0 to 10%) to afford 1.19 g of (l-6b); m/z 175.1 (M+H)⁺.

References:

PFIZER INC.;BENBOW, John William;LOU, Jihong;PFEFFERKORN, Jeffrey Allen;TU, Meihua Mike WO2010/29461, 2010, A1 Location in patent:Page/Page column 36-37