Triethylamine → HCID 9965687, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.2 g of (2R)-2-amino-4-(3-thienyl)-1-butanol, hydrochloride in 40 mL of ethanol, is combined with 1.1 mL of tert-butylisothiocyanate and 1 mL of triethylamine and magnetically stirred under inert atmosphere at a temperature of about 20° C., then heated for 20 hours at a temperature of about 50° C. The reaction medium is concentrated under reduced pressure (2 kPa) at a temperature of about 50° C. The solution is evaporated to obtain a residue, which is purified by chromatography under argon pressure (70 kPa), on a column of silica gel (particle size 60-200 μm; diameter 3.6 cm; height 20 cm), eluting with a mixture of cyclohexane-ethylacetate (60/40 by volume) and obtaining fractions of 30 mL. The fractions containing the expected product are collected and evaporated under reduced pressure (2 kPa) at a temperature of about 40° C. About 0.73 g of N-(tert-butyl)-N′-[(1R)-2-hydroxy-1-(2-thien-3-ylethyl)ethyl]thiourea are obtained in the form of a colorless oil. [1H NMR spectrum (300 MHz, (CD3)2SO d6, δ in ppm): 1.42 (s, 9H); from 1.60 to 1.95 (mt, 2H); 2.60 (t large, J=8 Hz, 2H); 3.38 (mt, 1H); 3.50 (mt, 1H); 4.26 (mf, 1H); 4.80 (mf, 1H); 7.01 (dd, J=5 and 1.5 Hz, 1H); from 7.15 to 7.25 (mt, 2H); 7.20 (s, 1H); 7.46 (dd, J=5 and 3 Hz, 1H)].

Provenance & Evidence