Urea → 1-(2-Chlorophenyl)-3-methylurea

HRID 2258485Notes

Reaction equation

HRID 2258485 reaction equation
ClC1C=CC=CC=1N=C=O.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]=[CH:36][C:35]=2[Cl:40])[C:32](=[O:41])[N:31](C)[C:30](=O)C=1.[H][H].ClC1C=CC=CC=1N1C(N)=C(N)C(=O)N(C)C1=O>>[CH3:30][NH:31][C:32]([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[Cl:40])=[O:41]

Participants

9

Reactant 8

HCID 1176UreaHCID 6329MethylamineHCID 9740Cyanoacetic acidHCID 76833Chlorophenyl isocyanateHCID 22922058HCID 22922058, compoundHCID 22922081HCID 22922081, compoundHCID 23668193Sodium NitriteHCID 178418361HCID 178418361, compound

Product 1

HCID 1399461-(2-Chlorophenyl)-3-methylurea

Procedure

N-Methyl-N'-(2-chlorophenyl)urea was prepared preliminarily from 2-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-(2-chlorophenyl)-3-methyluracil and then reduced with hydrogen gas to prepare 1-(2-chlorophenyl)-5,6-diamino-3-methyluracil.

Workup

  1. customto form a uracil ring

Sources & evidence

ORD record
ord-15c6fd0fdb604cbdbd8a09031720ab08
Source dataset
uspto-grants-1997_08
Patent number
US05661153

Reaction notes

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