Ethyl chloroformate → Diethyl imidazo[1,2-a]quinoxaline-2,5(4H)-dicarboxylate

HRID 358026Notes

Reaction equation

HRID 358026 reaction equation
[CH:1]1[N:5]2[C:6]3[C:11]([N:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][C:4]2=[N:3][CH:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[CH:1]1[N:5]2[C:6]3[C:11]([N:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][C:4]2=[N:3][C:2]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 20450291HCID 20450291, compound

Product 1

HCID 13228332Diethyl imidazo[1,2-a]quinoxaline-2,5(4H)-dicarboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.0 g of ethyl 4,5-dihydroimidazo[1,2-a]quinoxaline-5-carboxylate in 5 ml of dry dimethylformamide was treated with 0.5 g of ethyl chloroformate and the mixture was stirred at room temperature. After 2 hours, the mixture was set solid, was filtered and the residue was triturated with water and chromatographed over silica gel with ethyl acetate as eluant to obtain 0.98 g (76% yield) of diethyl 4,5-dihydroimidazo[1,2-a]quinoxaline-2,5-dicarboxylate melting at 151°-3° C.

Workup

  1. filtrationwas filtered
  2. customthe residue was triturated with water
  3. customchromatographed over silica gel with ethyl acetate as eluant

Sources & evidence

ORD record
ord-7ce5789654ae4942bacfe37cc941ecbf
Source dataset
uspto-grants-1984_08
Patent number
US04464373

Reaction notes

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