Urea → N-methyl-N'-(1-naphthyl)urea

HRID 2258487Notes

Reaction equation

HRID 2258487 reaction equation
C1(N=C=O)C2C(=CC=CC=2)C=CC=1.CN.NC(N)=O.C(CC(O)=O)#N.N([O-])=O.[Na+].NC1[N:36]([C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=[CH:39][CH:38]=2)[C:35](=[O:47])[N:34](C)[C:33](=O)C=1.[H][H].NC1C(=O)N(C)C(=O)N(C2C3C(=CC=CC=3)C=CC=2)C=1N>>[CH3:33][NH:34][C:35]([NH:36][C:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][CH:38]=1)=[O:47]

Participants

9

Reactant 8

HCID 1176UreaHCID 6329MethylamineHCID 9740Cyanoacetic acidHCID 66589alpha-Naphthyl isocyanateHCID 1649267HCID 1649267, compoundHCID 22922103HCID 22922103, compoundHCID 23668193Sodium NitriteHCID 178418361HCID 178418361, compound

Product 1

HCID 308345N-methyl-N'-(1-naphthyl)urea

Procedure

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

Workup

  1. customto form a uracil ring

Sources & evidence

ORD record
ord-4d2c159ee4514193b7e92e70a67f8a43
Source dataset
uspto-grants-1997_08
Patent number
US05661153

Reaction notes

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