ethyl {[(5-bromopyridin-2-yl)amino]carbonothioyl}-carbamate synthesis

Yield:1010120-60-1 100%

Reaction Conditions:

in dichloromethane at 5 - 20; for 16.25 h;

Steps:

2.1

Method 22.1 l-(5-Bromo-pyridin-2-yl)-3-carboethoxy-thiourea (2)To a solution of 2-amino-5-bromopyridine (1) (200.0 g, 1.156 mol) in DCM (2.0 L) cooled to 5 ⁰C was added ethoxycarbonyl isothiocyanate (134.9 mL, 1.156 mol) dropwise over 15 min. The reaction mixture was then allowed to warm to room temperature (20 ⁰C) and stirred for 16 h. Evaporation in vacuo gave a yellow solid which was collected by filtration, thoroughly washed with petrol (3 x 500 mL) and air-dried to afford the title compound (351.5 g, quantitative). No further purification was required.¹H NMR (de-DMSO) δ 12.22 (br s, IH), 11.75 (br s, IH), 8.66 (br s,lH), 8.57 (d, IH), 8.16 (dd, IH), 4.26 (q, 2H), 1.28 (t, 3H).

References:

WO2009/68482,2009,A1 Location in patent:Page/Page column 43