Urea → Urea, 1-(p-fluorophenyl)-3-methyl-

HRID 2258477Notes

Reaction equation

HRID 2258477 reaction equation
FC1C=CC(N=C=O)=CC=1.CN.NC(N)=O.C(CC(O)=O)#N.N([O-])=O.[Na+].NC1[N:33]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[C:32](=[O:41])[N:31](C)[C:30](=O)C=1.[H][H].NC1C(=O)N(C)C(=O)N(C2C=CC(F)=CC=2)C=1N>>[CH3:30][NH:31][C:32]([NH:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)=[O:41]

Participants

9

Reactant 8

HCID 1176UreaHCID 6329MethylamineHCID 9740Cyanoacetic acidHCID 709554-Fluorophenyl isocyanateHCID 15859067HCID 15859067, compoundHCID 229220036-Amino-1-(4-fluorophenyl)-3-methylpyrimidine-2,4(1H,3H)-dioneHCID 23668193Sodium NitriteHCID 178418361HCID 178418361, compound

Product 1

HCID 96348Urea, 1-(p-fluorophenyl)-3-methyl-

Procedure

N-Methyl-N'-(4-fluorophenyl)urea was prepared preliminarily from 4-fluorophenyl isocyanate and methylamine 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-3-methyl-1-(4-fluorophenyl)uracil and then reduced with hydrogen gas to prepare 5,6-diamino-1-(4-fluorophenyl)-3-methyluracil.

Workup

  1. customto form a uracil ring

Sources & evidence

ORD record
ord-b22e92406c9345efb16440fa9f2eabb2
Source dataset
uspto-grants-1997_08
Patent number
US05661153

Reaction notes

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