Dimethylformamide → HCID 18318497, compound

Participants

Reaction Conditions

Reaction Steps

To 50 ml. of dry DMF were added 1.2 g. (2.6 mmole) of the product from Example 16. Sodium hydride (625 mg.; 26 mmole) was added to the mixture under a nitrogen atmosphere. To the resulting mixture then were slowly added by syringe 620 mg. (10 mmole) of ethyl mercaptan. A vigorous effervescence occurred. When the effervescence had ceased, the reaction mixture was heated at 75° C. in an oil bath for 12 hours. Ethanol (5 ml.) then was added dropwise. The resulting mixture was evaporated to dryness, and the residue was dissolved in a mixture of ethyl acetate and water. The ethyl acetate layer was separated, washed with 50 ml. of aqueous sodium chloride solution, and then repeatedly with 15 ml. portions of 1N hydrochloric acid. The hydrochloric acid extracts were combined, washed with ether, and rendered alkaline by addition of cold 1N sodium hydroxide. The alkaline mixture then was extracted with ethyl acetate, and the ethyl acetate extract, after drying over magnesium sulfate, was evaporated to obtain 0.54 g. of a yellow oil. The yellow oil was chromatographed to obtain 400 mg. of the title compound as a yellow foam.

Provenance & Evidence