Urea → 1-Benzyl-3-phenylurea

HRID 2258479Notes

Reaction equation

HRID 2258479 reaction equation
C1(N=C=O)C=CC=CC=1.C(N)C1C=CC=CC=1.NC(N)=O.C(CC(O)=O)#N.N([O-])=O.[Na+].NC1[N:38]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:37](=[O:45])[N:36]([CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)C(=O)C=1.[H][H].C(N1C(=O)C(N)=C(N)N(C2C=CC=CC=2)C1=O)C1C=CC=CC=1>>[CH2:46]([NH:36][C:37]([NH:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:45])[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

9

Reactant 8

HCID 1176UreaHCID 7504BenzylamineHCID 7672Phenyl isocyanateHCID 9740Cyanoacetic acidHCID 2823049HCID 2823049, compoundHCID 22922029HCID 22922029, compoundHCID 23668193Sodium NitriteHCID 178418361HCID 178418361, compound

Product 1

HCID 2803631-Benzyl-3-phenylurea

Procedure

N-Benzyl-N'-phenylurea was prepared preliminarily from phenyl isocyanate and benzylamine 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-benzyl-1-phenyluracil and then reduced with hydrogen gas to prepare 3-benzyl-5,6-diamino-1-phenyluracil.

Workup

  1. customto form a uracil ring

Sources & evidence

ORD record
ord-c92e178cab9f42eaa0e5287229d6ae66
Source dataset
uspto-grants-1997_08
Patent number
US05661153

Reaction notes

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