N,N'-Dimethylurea → HCID 21501253, compound

Participants

Reaction Steps

A mixture of 88.1g (1.0 mole of 1,3-dimethylurea, 269.5g (1.0 mole) of tris(2-chloroethyl) phosphite, and 135g (1.05 moles) of 2-ethylhexaldehyde is warmed at 105°-110° for 2 hr, giving a clear colorless solution containing 2-(2-chloroethoxy)-1,4-dimethyl 3-(3-heptyl)-1,4,2-diazaphospholidin-5-one-2-oxide, as an intermediate ester product, 31P nmr 31 30.8. Four-fifths of the reaction mixture is dissolved in 200ml of cyclohexane containing 34.5g of H2O, and the mixture is warmed at 82° for 0.5 hr. Filtration after cooling, and extraction of the solid with hot acetonitrile gives 54.7g of white solid (100.8g more separates from the filtrate while standing): mp 184°-186° dec; 31P nmr (CD3SOCD3) -23.5 ppm(m); 1H nmr δ9.8 (broad, 2, OH), 4,4 (d of d, 1, J = 10 and 20Hz, PCH), 2.7 (s, 3, NCH3), 2.5 (s, 3, NCH3), 0.5 - 2.0 (broad, 15, hexyl); acidity 1.985 equiv/mole, pK1 = 1.76, pK2 = 5.29.

Provenance & Evidence