Urea → N-(3-chlorophenyl)-N'-methylurea

HRID 2258486Notes

Reaction equation

ClC1C=C(N=C=O)C=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][CH:37]=[C:36]([Cl:40])[CH:35]=2)[C:32](=[O:41])[N:31](C)[C:30](=O)C=1.[H][H].ClC1C=C(N2C(N)=C(N)C(=O)N(C)C2=O)C=CC=1>>[CH3:30][NH:31][C:32]([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=1)=[O:41]

Participants

Reactant 8

HCID 1176Urea

HCID 6329Methylamine

HCID 9740Cyanoacetic acid

HCID 17968Benzene, 1-chloro-3-isocyanato-

HCID 1649260HCID 1649260, compound

HCID 22922001HCID 22922001, compound

HCID 23668193Sodium Nitrite

HCID 178418361HCID 178418361, compound

Product 1

HCID 30384N-(3-chlorophenyl)-N'-methylurea

Procedure

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

Workup

customto form a uracil ring

Sources & evidence

ORD record: ord-933a010268e9401ab672f841eba005ef
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05661153

Reaction notes

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