Benzene, 1-chloro-3-isocyanato- → 1-(1-Benzyl-2-pyrrolidylidene)-3-(m-chlorophenyl)urea

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Reaction Steps

The fluoroborate salt of 1-benzyl-2-iminopyrrolidine (6.55 g.; 0.025 mole) is converted to free base (4.36 g.; 0.025 mole - assuming 100% conversion) by adding 5 ml. of 50% of NaOH to an aqueous slurry of the salt and benzene extraction. After drying over K2CO3, the benzene solution is filtered through diatomaceous earth and 3.84 g. (0.025 mole) of m-chlorophenylisocyanate, dissolved in anhydrous benzene, is added. The reaction mixture is stirred at room temperature for 2 hours and then taken to dryness in vacuo to give an oily residue which eventually crystallizes. Recrystallizations from acetone-petroleum ether affords a pure product, 1-(1-benzyl-2-pyrrolidylidene)-3-(m-chlorophenyl)urea, m.p. = 91°-93° C.

Provenance & Evidence