1,3-Propanedithiol → [5-(Trifluoromethyl)-1,2-oxazol-3-yl]methanamine

Participants

Reaction Steps

To a solution of 6.26 g 3-(azidomethyl)-5-(trifluoromethyl)isoxazole in 100 mL 2-propanol were added 9.08 mL triethyl amine and 330 uL 1,3-propanedithiol. 2.45 g sodiumhydride were added portion wise and stirred at RT for 16 h. The reaction mixture was concentrated in vacuo. The residue was poured carefully into 180 mL 10% acetic acid and washed with diethyl ether/heptane mixture 1.1 (3×50 mL) The aqueous layer was basified with conc. NaOH to pH=12 (50 mL), saturated with NaCl and extracted with CH2Cl2 (3×250 mL). The combined organic layer was dried over Na2SO4, filtered off and concentrated in vacuo to yield 3.4 g of the title compound as yellow oil; LC-MS (UV peak area/ESI) 97.6%, 167.043 (M+H)+.

Provenance & Evidence