C[O-].[Na+].[CH3:4][C:5]1[O:6][CH:7]=[CH:8][C:9]=1[SH:10].Cl[C:12]1[C:17]([CH2:18][CH:19]([CH3:21])[CH3:20])=[N:16][CH:15]=[CH:14][N:13]=1.Cl>CO.CCCCCC.O>[CH2:18]([C:17]1[C:12]([S:10][C:9]2[CH:8]=[CH:7][O:6][C:5]=2[CH3:4])=[N:13][CH:14]=[CH:15][N:16]=1)[CH:19]([CH3:21])[CH3:20]
Into a 25 ml round bottom 3 neck flask equipped with magnetic stirrer, Y tube, nitrogen inlet, and reflux condenser with calcium chloride drying tube is placed a solution of 0.15 g (0.0028 moles) of sodium methoxide in 2 ml absolute methyl alcohol. To the sodium methoxide solution, while maintaining the temperature at 22° - 25° C, is added 0.32 g (0.0028 moles) of 2-methyl-3-furan thiol dissolved in 2 ml absolute methanol. The reaction mass is stirred for a period of 10 minutes at 22° - 25° C at which time a solution of 0.43 g (0.0025 moles) of 2-chloro-3-isobutyl-pyrazine in 2 ml absolute methanol is added dropwise over a period of 2 minutes. The reaction mass is then heated to reflux at 65° C under nitrogen and maintained at reflux for a period of 4 hours. At the end of the 4 hour reflux period, the reaction mass is cooled to room temperature. 10 ml of water is added to the reaction mass which is then neutralized to a pH of 5 with dilute hydrochloric acid. Two 7 ml portions of n-hexane are then used to extract the reaction mass. The hexane layers are separated, combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated to a red amber oil weighing 0.51 g. The major material is isolated using GLC techniques (conditions: 8 feet × 1/4inche SE-30 column) and is confirmed by NMR, IR and Mass Spectral Analysis to be a material having the structure: ##SPC15##
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