Triethylamine → HCID 19862602, compound

Participants

Reaction Steps

5.60 ml of triethylamine are added to a mixture of 5.49 g of 3-hydroxy-1-(2-methoxyethyl)-2-methyl-4(1H)-pyridinone in 150 ml of acetonitrile and 150 ml of methylene chloride, followed by the addition of 6.83 ml of ethyl isocyanatoacetate at room temperature. The slightly exothermic reaction, in the course of which a solution forms within 10 minutes, is complete after 3 hours. The solvent is removed under reduced pressure and the residue is dried under a high vacuum and crystallised from ethyl acetate. The mother liquor is discarded. 1 g of the pale beige product is partitioned between methylene chloride and water. The bulk of the product is present in the aqueous phase, which is concentrated by evaporation. The residue is dissolved in methanol and the solution is treated with activated carbon and concentrated by evaporation. The residue is crystallised from ethyl acetate, to give white crystalline 3-(ethoxycarbonylmethylaminocarbonyloxy)-1-(2-methoxyethyl)-2-methyl-4(1H)-pyridinone with a melting point of 134°-135° C.

Provenance & Evidence