Sodium hydride → HCID 70695469, compound

Participants

Reaction Steps

Sodium hydride (0.447 g, 17.71 mmol) was added portionwise to a suspension of 4-{[(3-chloro-2-methylphenyl)methyl]amino}-2-(4-morpholinyl)-1,3-thiazole-5-carboxamide (0.812 g, 2.213 mmol) and 1,1′-thiocarbonyldiimidazole (1.183 g, 6.64 mmol) in Tetrahydrofuran (THF) (20 mL). The mixture was stirred at rt for 2.5 days, then quenched by the dropwise addition of saturated NH4Cl solution. The solvent was evaporated in vacuo and the residue was suspended in water. The pH was adjusted to about 6 by the addition of 1 N HCl. The yellowish orange solid was collected by filtration, washed with water, and dried in a vacuum oven at 65 C to provide 887 mg of the titled compound (98% yield). LC/MS: MS (ES+) m/e 409 (MH+)

Provenance & Evidence