Sodium hydride → HCID 53823975, compound

Participants

Reaction Steps

2-(Cyanoimino)thiazolidine (6.35 g, 49.9 mmol), prepared by the procedure of Neidlein and Reuter, Arch. Pharm. (Weinheim, Ger.) 305, 731 (1972), was added to a suspension of sodium hydride (2.04 g, 51 mmol, pre-washed with hexane)in dimethylformamide (100 mL) at ambient temperature, resulting in heat and gas evolution. After stirring the mixture 30 minutes, tert-butyl bromoacetate (10.0 g, 51.3 mmol) was added and the resulting mixture was stirred 2.5 hours at ambient temperature. After removing the solvent in vacuo, the residue was partitioned between saturated sodium bicarbonate and methylene chloride and the aqueous phase extracted with additional methylene chloride (2×). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. Subsequent recrystallization from methylene chloride/hexane (1:4) afforded 9.04 g (75%) of the title compound as a white crystalline solid. m.p. 143°-144° C. TLC (ethyl acetate) Rf =0.44. 1H NMR (CDCl3, 300 MHz) d 1.48 (s, 9H), 1.48 (s, 9H), 3.43 (t, 2H), 3.98 (t, 2H), 4.08 (s, 2H). MS (DCl/NH3) m/e 242 (M+H)+. Anal calcd for C10H15N3O2S.0.25 H2O: C, 48.86; H, 6.36; N, 17.09. Found: C, 48.71; H, 5.98; N, 16.93.

Provenance & Evidence