Propane sultone → 1-(3-Sulfonylpropyl)-2,5-dimethylpyrazine

Participants

Reaction Conditions

Reaction Steps

6.0 g of 2,5-dimethylpyrazine (701) and 7.0 g of 1,3-propane sultone were dissolved in 10 ml of ethyl acetate and heated at 40° C. for 2 days. The resultant solid was then filtered and washed with ethyl acetate giving 7.9 g of product (700). It was recrystallized from propanol/water, m.p. 258°-9°. UV H2O max: 204 (3.94), 290 (3.85). 13C NMR: 159.25, S (C5); 152.47, D (C3); 146.91, S (C2); 136.88, D (C6); 57.84, T (NCH2); 47.94, T (CH2SO3-); 25.42, T (CH2); 21.49, Q, 17.16, Q (ArCH3). 1H NMR: 9.15, S (H3); 8.83, S (H6); 4.77, T (NCH2); 3.09, T (CH2SO3-), 2.90, S, 2.75, S (ArCH3); 2.40, M=5 (--CH2 --).

Provenance & Evidence