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

Temperature

0 °C

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.

1. additionwas added
2. dissolutionthe solid slowly dissolving
3. waitthe reaction mixture was left
4. waitto stand for 60 hours
5. customThe mixture was evaporated under reduced pressure
6. customto afford an oily residue, which
7. customgave a solid which
8. filtrationwas collected by filtration
9. customdried

ORD record

ord-0bff15197bda4a2c9b15ec2a40156d2e

Source dataset

uspto-grants-1985_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04521625