1-Dodecanethiol

• Nosylamide 1
• 1-Dodecanethiol [D0970]
• K₂CO₃ [P1748]
• Acetonitrile

A solution of nosyl amide 1 (384 mg, 0.95 mmol), 1-dodecanethiol (339 µL, 1.42 mmol, 1.5 eq.) and K₂CO₃ (197 mg, 1.42 mmol, 1.5 eq.) in MeCN (4.7 mL) were stirred for one day at 50 °C. 1-Dodecanethiol (339 µL, 1.42 mmol, 1.5 eq.) and K₂CO₃ (197 mg, 1.42 mmol, 1.5 eq.) were further added and the mixture was stirred for one day at 50 °C, then for one more day at 70 °C. Water (10 mL) was added to the reaction mixture and extracted with dichloromethane (4 x 10 mL). The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate:hexane = 5:95 - 33:67 - 50:50 on silica gel) to give amine 2 as a pale yellow oil (117 mg, 56% yield).

The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:1, Rf = 0.10).
1-Dodecanethiol has slightly bad smell, so that it was handled in a draft chamber.

Amine 2

¹H NMR (270 MHz, CDCl₃); δ 7.24 (brd, J = 8.8 Hz, 2H), 6.86 (brd, J = 8.8 Hz, 2H), 5.51-5.30 (m, 2H), 3.80 (s, 3H), 3.72 (s, 2H), 2.63 (t, J = 7.3 Hz, 2H), 2.08 (brq, J = 7.0 Hz, 2H), 1.64-1.52 (m, 5H), 1.49 (brs, 1H).

• Application of Odorless Thiols for the Cleavage of 2-and 4-Nitrobenzenesulfonamides
• M. Matoba, T. Kajimoto, M. Node, Synth. Commun. 2008, 38, 1194.