Toluene → HCID 14347815, compound

Participants

Reaction Steps

Two drops of N,N-dimethylformamide were added to a mixture of 4-carbamoylmethyl-7-fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one (1.4 g), thionylchloride (1.2 g) and toluene (20 ml), and the mixture was stirred at a temperature of 100° C. to 110° C. for 6 hours. After the liquor was allowed to cool, methylisobutyl ketone (300 ml) was added thereto, and the liquor was washed with water, a saturated aqueous solution of sodium bicarbonate, water and a saturated table salt solution, in that order, subsequently dried with anhydrous sodium sulfate. After the solvent was distilled off, toluene (300 ml) and activated carbon (0.5 g) were added to the residue, the mixture was heated for a minute, and filtered while it was still hot. The resulting product was allowed to stand overnight, resulting crystals were recovered by filtration, and dried to give the desired 4-cyanomethyl-7-fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one (0.64 g). When the residue obtained by distilling the mother liquor was recrystallized from a minimum amount of toluene, an additional amount (0.3 g) of the desired compound was produced. mp. 196°-200° C.

Provenance & Evidence