Urea → 2-Ethyl-1-ureidohexylphosphonic acid

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Reaction Steps

This compound is prepared from urea, tris(2-chloroethyl) phosphite, 2-ethylhexaldehyde, and water under conditions similar to those used for the preparation of 1-ureidopropyl-phosphonic acid in Example 4. The product is obtained as a white solid: mp 206° C dec; 31P nmr (CD3SOCD3) -23.2 ppm; 1H nmr δ8.5 (broad, 4, HO and NH2), 6.2 (d, 1, J = 8Hz, NH), 4.3 (d, of d, 1, J = 8 and 20Hz, PCH), 1.3 and 0.9 (m, 15); acidity 2.00 equiv/mole, pK1 = 3.50, pK2 = 9.08.

Provenance & Evidence