Urea → N-Methyl-N'-(4-chlorophenyl)urea

HRID 2258484Notes

Reaction equation

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

Participants

Reactant 8

HCID 1176Urea

HCID 6329Methylamine

HCID 76934-Chlorophenyl Isocyanate

HCID 9740Cyanoacetic acid

HCID 2513996-amino-1-(4-chlorophenyl)-3-methylpyrimidine-2,4(1h,3h)-dione

HCID 11737217HCID 11737217, compound

HCID 23668193Sodium Nitrite

HCID 178418361HCID 178418361, compound

Product 1

HCID 79309N-Methyl-N'-(4-chlorophenyl)urea

Procedure

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

Workup

customto form a uracil ring

Sources & evidence

ORD record: ord-cb4d7118b0b64e86bc6874208b9d63f6
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05661153

Reaction notes

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