Urea → 2-Ethyl-1-ureidohexylphosphonic acid

HRID 1415281

Reaction equation

HRID 1415281 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].[P:5]([O:14]CCCl)([O:10]CCCl)[O:6]CCCl.[CH2:18]([CH:20]([CH2:23][CH2:24][CH2:25][CH3:26])[CH:21]=O)[CH3:19].N(C(P(=O)(O)O)CC)C(N)=O>O>[CH2:18]([CH:20]([CH2:23][CH2:24][CH2:25][CH3:26])[CH:21]([P:5](=[O:6])([OH:10])[OH:14])[NH:1][C:2]([NH2:4])=[O:3])[CH3:19]

Participants

6

Reactant 4

HCID 1176UreaHCID 8783Tris(2-chloroethyl) phosphiteHCID 312412-EthylhexanalHCID 214840221-Ureidopropyl-phosphonic acid

Product 1

HCID 214840232-Ethyl-1-ureidohexylphosphonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. customThe product is obtained as a white solid

Sources & evidence

ORD record
ord-59b4a74bb06e49629d5405ceded3fef5
Source dataset
uspto-grants-1977_01
Patent number
US04003965

Linked notes

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