Water → 3-Amino-4-[(3-chloropropyl)amino]cyclobut-3-ene-1,2-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-amino-2-(3-hydroxypropylamino)cyclobut-1-ene-3,4-dione (1.0 g) and pyridine (0.5 ml) in chloroform (100 ml) was cooled to 0° C. To this was added dropwise thionyl chloride (4.38 g) in chloroform (30 ml) and the reaction mixture was stirred overnight at room temperature. There was solid remaining so more thionyl chloride (4.38 g) was added, the solid slowly dissolving, and the reaction mixture was left to stand for 60 hours. The mixture was evaporated under reduced pressure to afford an oily residue, which on the addition of water gave a solid which was collected by filtration and dried to give the title compound (0.73 g); δppm 2.0 (2H, m), 3.5-3.8 (4H, m), 7.45 (broad m); m/e 190, 188, 152, 134, 132, 97, 96, 69.

Provenance & Evidence