Sodium Azide → 4-azido-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

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A solution of 4-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran (6.73 g, 25.29 mmoles), title B compound, in dry N,N-dimethylformamide (100 mL) was treated with sodium azide (3.79 g, 50.57 mmoles) and stirred at room temperature under argon for 4 hours. The reaction mixture was partitioned between 100 mL ethyl acetate and 200 mL distilled water. The organic layer was separated and the aqueous layer was extracted with 100 mL of ethyl acetate. The combined organics were washed successively with distilled water, saturated sodium bicarbonate solution, brine and dried over magnesium sulfate. The solvent was evaporated under vacuum to obtain an orange gum (5.62 g) which was triturated with pentane to provide the title compound (4.50 g, 78%) as an off-white solid, m.p. 63°-64° C. Microanalysis calculated for C12H12N4O: C, 63.15; H, 5.30; N, 24.55. Found: C, 63.57; H, 5.27; N, 24.75.

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