Hexamethylenetetramine → HCID 69542107, compound

Participants

Reaction Conditions

Reaction Steps

3-methyl-1-(5-methyl-4-phenyl-(2-thienyl))butan-1-one (106 g, 0.411 mol), urotropin (161.2 g, 1.15 mol), and acetic anhydride (151.1 g, 1.48 mol) were mixed in a 1 L flask, sparged with nitrogen, and stirred for 24 h at 110° C. The dark mixture was cooled to 70° C. and poured into 700 mL of a 2 N aqueous solution of NaOH. The organic fraction was extracted with 50/50 (v/v) dichloromethane/hexane (3×250 mL), washed with 1 N HCl, saturated aqueous solution of NaHCO3, and dried (MgSO4). Evaporation of solvents gave 98 g of crude product (70% product by GC/MS) used without further purification. 1H-NMR δ (CDCl3): 7.5 (s, 1H), 7.2–7.38 (m, 5H), 5.6 (s, 1H), 5.45 (s, 1H), 2.9 (m, 1H), 2.41 (s, 3H), 1.05 (d, 6H). EIMS: m/z (%) 270 (M+, 65), 255 (100), 237 (11), 201 (89), 171 (11), 129 (38).

Provenance & Evidence