Ethyl 2-(furan-2-ylmethylidene)-3-oxobutanoate → 5-Methyl-7-(2-furyl)-1,2,3,7-tetrahydroimidazolo[1,2-a]pyridine-6,8-dicarboxylic acid diethyl ester

HRID 972878Notes

Reaction equation

HRID 972878 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5](=[CH:9][C:10]1[O:14][CH:13]=[CH:12][CH:11]=1)[C:6]([CH3:8])=O)[CH3:2].[C:16]([CH:21]=[C:22]1[NH:26][CH2:25][CH2:24][NH:23]1)([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[CH:9]([C:10]2[O:14][CH:13]=[CH:12][CH:11]=2)[C:21]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:22]2[NH:23][CH2:24][CH2:25][N:26]2[C:6]=1[CH3:8])=[O:15])[CH3:2]

Participants

4

Reactant 2

HCID 252577Ethyl 2-(furan-2-ylmethylidene)-3-oxobutanoateHCID 12377942Ethyl (imidazolidin-2-ylidene)acetate

Product 1

HCID 681190535-Methyl-7-(2-furyl)-1,2,3,7-tetrahydroimidazolo[1,2-a]pyridine-6,8-dicarboxylic acid diethyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Boiling a solution of 6.9 g of 2-furfurylideneacetoacetic acid ethyl ester and 5.2 g of 2-carbethoxymethylideneimidazolidine in 50 ml of ethanol for 8 hours yields 5-methyl-7-(2-furyl)-1,2,3,7 -tetrahydroimidazolo[1,2-a]pyridine-6,8-dicarboxylic acid diethyl ester of melting point 164° (ethanol).

Workup

  1. customfor 8 hours

Sources & evidence

ORD record
ord-a3c8c37307684b7faec326511ee5b8b9
Source dataset
uspto-grants-1977_10
Patent number
US04053614

Reaction notes

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