Valeronitrile → HCID 178441990, compound

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Reaction Steps

Following the procedure described in Example 21, valeronitrile (845 mg, 10.16 mmol) was reacted with dibutyltin oxide (254 mg, 1.02 mmol) and trimethylsilyl azide (2.70 ml, 19.8 mmol) in toluene (20 mL) to give 1.088 g (85%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ0.95 (t, J=7 Hz, 3H), 1.43 (sextet, J=7 Hz, 2H), 1.87 (pentet, J=7 Hz, 2H), 3.12 (t, J=7 Hz, 2H). 13C NMR (CDCl3, 75 MHz) 13.42, 22.04, 23.08, 29.62, 156.94. IR (CDCl3) 2900, 1555 cm-1. MS (DCl/NH3) m/e 127 (M+H)+, 144 (M+H+NH3)+. Anal calcd for C5H10N4 : C, 47.60; H, 7.99; N, 44.41. Found: C, 47.14; H, 7.99; N, 43.75.

Provenance & Evidence