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0 °C

3-(2-(1-pyrrolidinyl)-2-oxoethyl)-4,5-dimethyl-thiazolium chloride was prepared from the reaction of N-(chloroacetyl)pyrrolidine with 4,5-dimethylthiazole. N-(chloroacetyl)pyrrolidine was prepared as follows. Pyrrolidine (63.9 g. 0.9 mol) was taken in methylene chloride (640 mL) and cooled to 0° C. in a salt-ice bath. To the stirred mixture was added chloroacetyl chloride (101.8 g in 450 mL of CH2Cl2, 0.9 mol) dropwise keeping the inside temperature below 15° C. After adding the chloroacetyl chloride, the mixture was stirred for an hour at 5° C. Sodium hydroxide solution (7 M, 190 mL) was added with vigorous stirring such that the inside temperature did not exceed 20° C. The mixture was stirred for 15 minutes and the aqueous layer was separated. The organic layer was washed successively with saturated sodium bicarbonate solutions (2×200 mL), water (1×200 mL) and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was recrystallized from hexane to give 64.5 g (48.6%) of white plate crystals, m.p. 43° C.

1. customthe inside temperature below 15° C
2. stirringwith vigorous stirring such that the inside temperature
3. customdid not exceed 20° C
4. stirringThe mixture was stirred for 15 minutes
5. customthe aqueous layer was separated
6. washThe organic layer was washed successively with saturated sodium bicarbonate solutions (2×200 mL), water (1×200 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. customThe solvent was removed in vacuo
9. customthe residue was recrystallized from hexane
10. customto give 64.5 g (48.6%) of white plate crystals, m.p. 43° C.