Ethyl orthoformate → HCID 54311975, compound

HRID 544202Notes

Reaction equation

HRID 544202 reaction equation
[C:1]([CH2:6][C:7]([NH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8])([O:3][CH2:4][CH3:5])=[O:2].[CH:15](OCC)(OCC)[O:16][CH2:17][CH3:18]>C(OC(=O)C)(=O)C>[C:1]([C:6](=[CH:15][O:16][CH2:17][CH3:18])[C:7]([NH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8])([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 2822005HCID 2822005, compound

Product 1

HCID 54311975HCID 54311975, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Following the procedure of Example 1, N-(2-carbethoxyacetyl)urethane is reacted with triethyl orthoformate in acetic anhydride to give α-carbethoxy-β-ethoxy-N-ethoxycarbonylacrylamide. This is reacted with 2,4,6-trichlorophenylhydrazine, giving α-carbethoxy-β-(2,4,6-trichlorophenylhydrazino)-N-ethoxycarbonylacrylamide which is cyclized to yield 5-carbethoxy-1-(2,4,6-trichloroanilino)-2,4-pyrimidinedione.

Sources & evidence

ORD record
ord-37cd76274fa54c878b2599632603d66c
Source dataset
uspto-grants-1984_05
Patent number
US04448961

Reaction notes

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