Urea → Urea, N-phenyl-N'-propyl-

HRID 2258478Notes

Reaction equation

HRID 2258478 reaction equation
C1(N=C=O)C=CC=CC=1.C(N)CC.NC(N)=O.C(CC(O)=O)#N.N([O-])=O.[Na+].N[C:29]1[N:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:33](=[O:41])[N:32](CCC)[C:31](=O)[CH:30]=1.[H][H].NC1C(=O)N(CCC)C(=O)N(C2C=CC=CC=2)C=1N>>[CH2:31]([NH:32][C:33]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:41])[CH2:30][CH3:29]

Participants

9

Reactant 8

HCID 1176UreaHCID 7672Phenyl isocyanateHCID 7852PropylamineHCID 9740Cyanoacetic acidHCID 158590685,6-Diamino-1-phenyl-3-propylpyrimidine-2,4(1H,3H)-dioneHCID 229220916-Amino-1-phenyl-3-propylpyrimidine-2,4(1H,3H)-dioneHCID 23668193Sodium NitriteHCID 178418361HCID 178418361, compound

Product 1

HCID 3604138Urea, N-phenyl-N'-propyl-

Procedure

N-Propyl-N'-phenylurea was prepared preliminarily from phenyl isocyanate and propylamine by the same procedure as in Reference Example 1. The urea compound as the starting material was reacted with cyanoacetic acid to form a uracil ring. Using sodium nitrite a nitroso group was introduced into the 5-position of the uracil ring in the obtained 6-amino-1-phenyl-3-propyluracil and then reduced with hydrogen gas to prepare 5,6-diamino-1-phenyl-3-propyluracil.

Workup

  1. customto form a uracil ring

Sources & evidence

ORD record
ord-63a3d71f38ba47f682fe485b3b780e32
Source dataset
uspto-grants-1997_08
Patent number
US05661153

Reaction notes

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