8 18 m 4h m p 200 u00b0 200 5 u00b0 c found c 33 56 h 4 13 n 3 88 c 10 h 15 no 7 s 3 requires c 33 60 h 4 23 n 3 92 4 2 hydroxyethylsulfonyl phenylsulfonylmethanesulfonamide m p 198 5 u00b0 200 0 u00b0 c was prepared similarly from the corresponding hydroxyethylthio compound thiophene 6 9 ml and 75 ml of ether were mixed under an atmosphere of nitrogen n butyl lithium 60 ml 1 6m in hexane was added dropwise and the mixture was refluxed for 1 hour the reaction mixture was cooled to 65 u00b0 c and 2 8 g of elemental sulfur was added the reaction mixture was stirred at 70 u00b0 c for 45 minutes and then allowed to warm to room temperature the ether solvent was removed under vacuum and 50 ml of dimethylformamide was added bromomethanesulfonamide 15 g was added and the reaction mixture was heated to 80 u00b0 c after 1 5 hours at 80 u00b0 c the reaction mixture was cooled to room temperature and the dmf was removed under vacuum hydrochloric acid 1n and ethyl acetate were added to the oily residue the ethyl acetate phase was separated and washed with brine dried over sodium sulfate and concentrated under vacuum the resultant oil was chromatographed using 230 400 mesh silica gel and eluting with 1 1 ethyl acetate hexane yield 11 3 g of solid 62 8 n m r cdcl 3 300 mhz u03b4 4 26 s 2h 5 13 brs 2h 7 02 m 1h 7 38 m 1h 7 46 d 1h a solution of 11 0 g of 2 thienylthiomethanesulfonamide in 200 ml of acetonitrile was prepared and 9 1 ml 1 3 equivalents of dimethylformamide dimethylacetal added after.