Aniline → Formanilide

HRID 466308

Reaction equation

HRID 466308 reaction equation
[C:1]1([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18].[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>[Ru]>[C:11]1([NH:10][C:8]([NH:7][C:1]2[CH:2]=[CH:3][C:4]([CH3:17])=[CH:5][CH:6]=2)=[O:9])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18].[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:1])=[CH:29][CH:28]=1

Participants

7

Reactant 3

HCID 6115AnilineHCID 7595CarbanilideHCID 7671Formanilide

Product 3

HCID 7671FormanilideHCID 7813p-ToluidineHCID 5721701-(4-Methylphenyl)-3-phenylurea

Reagents, catalysts & solvents 1

HCID 23950RutheniumCatalyst

Procedure

Watanabe et al. (J. Chem. Soc., Chem. Commun. (1990) 1497) reported a synthesis of N,N'-diphenylurea in 92% yield by dehydrogenating formanilide in the presence of aniline and a ruthenium catalyst: ##STR2## Watanabe et al. prepared numerous symmetric N,N'-diarylureas in this manner. In contrast, N-phenyl-N'-p-tolylurea was not obtained selectively from the reaction of formanilide and p-toluidine. Instead, a mixture of three ureas -- N,N'-diphenylurea (19%), N,N'-di-p-tolylurea (21%), and the unsymmetric product, N-phenyl-N'-p-tolylurea (38%) -- was obtained:

Sources & evidence

ORD record
ord-3f4e9027ed884b30bddbbede4b6e84d6
Source dataset
uspto-grants-1992_10
Patent number
US05155267

Linked notes

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