Acetic Anhydride → Ethyl (2-cyano-3-ethoxybut-2-enoyl)carbamate

HRID 648161Notes

Reaction equation

[CH2:1]([O:3][C:4]([NH:6][C:7](=[O:11])[CH2:8][C:9]#[N:10])=[O:5])[CH3:2].[C:12](OCC)(OCC)([O:14][CH2:15][CH3:16])[CH3:13].C(OC(=O)C)(=O)C>>[C:9]([C:8](=[C:12]([O:14][CH2:15][CH3:16])[CH3:13])[C:7]([NH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:11])#[N:10]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 23112N-Cyanoacetylethylcarbamate

HCID 66221Triethyl orthoacetate

Product 1

HCID 53396675Ethyl (2-cyano-3-ethoxybut-2-enoyl)carbamate

Procedure

Following the method of Example 1, N-ethoxycarbonylcyanoacetamide is heated with triethyl orthoacetate and acetic anhydride to give α-cyano-β-ethoxy-β-methyl-N-ethoxycarbonylacrylamide, which in turn is reacted with 2,4,6-trichlorophenylhydrazine. The resulting compound α-cyano-β-methyl-β-(2,4,6-trichlorophenylhydrazino)-N-ethoxycarbonylacrylamide (m.p.=183°-184°) is cyclized, yielding 5-cyano-6-methyl-1-(2,4,6-trichloroanilino)-2,4-pyrimidinedione, m.p.=>305°.

Sources & evidence

ORD record: ord-d93fbf8385384feca6312082d95102f6
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04411839

Reaction notes

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