1H-Imidazole-1-carbothioic acid, O-propyl ester synthesis

Yield:175538-78-0 94%

Reaction Conditions:

in MTBE (methyl tert-butyl ether) at 25 - 28; for 1 h;

Steps:

1; I

To the suspension of K '-thiαcai-tonyldiimidazole (3l .fi g, 177.3 jnmol) methyl tert-buyl eiher (MTBB, 95 rnL) at 25X is added -propanol ( I . .7 g, 14.6 mi, 195 mmol j. Wiihi.n . hour the reuction n-iixtυrc ra^phes 2ST and becoiiies a clear solution. TLC analysis (SiO₂, EiOAc eluem, Rf of the pruduct. 0.75; Rf of the starting material, 0.15) shows hsi the reaction is complete. Ti*.' reactsoR ^jiikfυrc is partis iosied between water (75 mL) and MTBE (25 inL). The organic phλtse is waskxi vsih wascf (75 ;L⁾, is ?ai?.inUSDt.cd sodium bicarhonaie soluiion (50 mt). brine (50 ?iL_.} and is conce trated OR a roSiis-y evaporate to an amber oil. compound 7 QS.5 g. 94% yield), AnaS. Calculated for C%H_S.iN,OS: C 49.39^; I L 5.92; N, 16.46. Found; C 49.47; H. 6.06: N, 16-50. JiPLC purity W..4K by area at 225 nrs (R_x -. 2.5 min). MS (ES+) m/x I T i 1II NMR (300 MBK, QXI_J) δS.33 (n, I H), 7.62 (m. I BJ, 7.02 {m, I H). 4.61 (ι, 2H), . ,'λ) (ffi 2H), l.O [t, 3H). DSC; 1_λ,, ,^ ^s)5^ciC, i 5 /9 W / ks s. Nose: J he maical should be stored in refrigerator and nzed wsthht ^'"' days. tfp?Jonged storage is necessary it is recommended u> keep it m a MTBE solution.

References:

WO2007/118010,2007,A1 Location in patent:Page/Page column 8; 10