Carbon Dioxide → HCID 131712980, compound

Participants

Reaction Steps

A 300-ml flask was charged with 12.1 g (0.05 mol) of 2-amino-4,5,6,7-tetrahydro-1H-1,3-diazepine hydroiodide 1), 10.0 g of 50% NaOH and 70 ml of THF. After stirring at room temperature for 1 hour, 10.0 g Na2SO4 was added and the mixture was stirred for an additional 1.5 hours. The reaction mixture was cooled to -30° C. (2-PrOH, dry ice) and a solution of 6.3 g (0.033 mol) of 2,6-dichlorophenyl isocyanate in 80 ml of THF was added over a period of 2 hours. At the end of addition, the reaction mixture was allowed to warm to room temperature and stirring continued for 1 hour. The solids, were filtered and the filtrate evaporated in vacuo. The residue was dissolved in dilute HCl, insolubles removed by filtration, and the aqueous solution washed with ether, made basic with cold 30% NaOH, and extracted with CH2Cl2. The combined organic layers were dried (K2CO3), filtered through a pad of diatomaceous earth and evaporated in vacuo. The residue was dissolved in MeOH, neutralized with ethereal HCl and treated with ether to give crystals which were recrystallized from MeOH/ether and then from a minimum amount of H2O to give pure N-(2,6-dichlorophenyl)-N'-(4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl)urea monohydrochloride hemihydrate; m.p. (175) 177°-179° C. dec. UV max. (MeOH) 244 (ε20,100) and 224 nm shld (ε20,800); IR (KBr) 3420, 3200, 1710, 1675, 1535 cm-1.

Provenance & Evidence