Ethanol → HCID 178431969, compound

Participants

Reaction Steps

To 4.60 g (15.1 mmole) of 2-guanidino-4-[(2-aminoethyl)thiomethyl]thiazole dihydrochloride stirred under flowing nitrogen in 170 ml of dry pyridine is added 1.38 g (ca. 30.3 mmole) of a 50 percent dispersion in oil of sodium hydride. After about 1 hour 2.80 g (15.0 mmole) of 2-carbethoxyamino-4-methylthiazole is added, and the resultant mixture is heated at reflux for 2 days. After partial cooling, the mixture is decanted through a sintered glass funnel using suction, all residues being discarded, and the filtered supernatant is concentrated in vacuo to a thick gum. Residual mineral oil is removed by trituration with several portions of diethyl ether and pentane, and the residue is purified by column chromatography* on silica gel. Fractions containing the product are combined, partially concentrated, filtered, and thoroughly dried by concentration in vacuo, giving 1.20 g (3.1 mmole) of the desired product as an ethanol solvate. Structure assignment and solvation by one quarter mole of ethanol per mole of product are supported by nmr.

Provenance & Evidence