Pyridine → HCID 20397536, compound

Participants

Reaction Steps

C6F13CH2CH2SCH2CH2OH (40.1 g, 0.094 mole, undistilled), acetic anhydride (16.2 g, 0.15 mole) and pyridine (0.98 g, 12.4 mmole) was heated at 65°-66° for 4 hours and 89° for 17 hours under total reflux. A sample after 4 hours showed incomplete reaction and after 17 hours, only a trace of C6F13CH2CH2SCH2CH2OH was present (GC analysis). The product was washed with saturated sodium bicarbonate (20 ml), extracted into ether, dried and the solvent removed by distillation; wt. 47.77 g. Total product was 49.3 g, 100% of theory. NMR was consistent for structure: proton resonances at 2.03 ppm, 3 protons, s, CH3 ; at 2.42 ppm, multiplet, 2 protons, CH2A ; at 2.78 ppm, multiplet, 4 protons, CH2A ; at 2.78 ppm, multiplet, 4 protons, CH2B and CH2C ; and at 4.24 ppm, t, 2 protons CH2D for C6F13CH2ACH2BSCH2CCH2DO2CCH3.

Provenance & Evidence