Hexanenitrile → HCID 178442321, compound

A mixture of hexanenitrile (938 mg, 9.65 mmol), dibutyltin oxide (293 mg, 0.98 mmol) and 97% trimethylsilylazide (2.60 mL, 19.1 mmol) in toluene (20 mL) were heated at ~110° C. for 25 hours and ambient temperature for one hour. The reaction mixture was extracted with 1M sodium hydroxide solution (4×10 mL) and the combined aqueous extracts were acidified with 6M hydrochloric acid to pH 3-4 and extracted with 10% isopropanol in chloroform (3×10 mL). The combined organic extracts were washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford 950 mg (70%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ0.87 (t, J=7 Hz, 3H), 1.30-1.45 (m, 4H), 1.90 (pentet, J=7 Hz, 2H), 3.12 (t, J=7 Hz, 2H). 13C NMR (CDCl3, 75 MHz) 13.70, 22.06, 23.35, 27.31, 31.05, 156.97. IR (CDCl3) 2900, 1555 cm-1. MS (DCl/NH3) m/e 141 (M+H)+, 158 (M+H+NH3)+. Anal calcd for C6H12N4 : C, 51.41; H, 8.63; N, 39.97. Found: C, 51.25; H, 8.59; N, 39.93.

1. extractionThe reaction mixture was extracted with 1M sodium hydroxide solution (4×10 mL)
2. extractionextracted with 10% isopropanol in chloroform (3×10 mL)
3. washThe combined organic extracts were washed with brine
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated in vacuo

ORD record

ord-05f150369ad24162a7b5e610fdc29f79

Source dataset

uspto-grants-1994_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05284954