Phenylhydrazine → HCID 70515097, compound

HRID 648165Notes

Reaction equation

[C:1]([C:3](=[CH:12]OCC)[C:4]([NH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])#[N:2].[C:16]1([NH:22][NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:1]([C:3](=[CH:12][NH:23][NH:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:4]([NH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])#[N:2]

Participants

Reactant 2

HCID 7516Phenylhydrazine

HCID 230015ethyl N-(2-cyano-3-ethoxyacryloyl)carbamate

Product 1

HCID 70515097HCID 70515097, compound

Procedure

Following the procedure of Example 1, α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide is reacted with phenylhydrazine to give α-cyano-β-phenylhydrazino-N-ethoxycarbonylacrylamide, which in turn is cyclized by heating in tetralin, yielding 5-cyano-1-anilino-2,4-pyrimidinedione. The foregoing compound has been reported by G. Shaw, J. Chem. Soc., 1955, 1834-1840.

Sources & evidence

ORD record: ord-89e70e89171b4d689a3b83b564732d0b
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04411839

Reaction notes

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