8871. Succinimide

Nomenclature

CAS number: 123-56-8
2,5-Pyrrolidinedione; butanimide; 2,5-diketopyrrolidine; 3,4-dihydropyrrole-2,5-dione; dihydro-3-pyrroline-2,5-dione; 2,5-dioxopyrrolidine; Orotric (SAT).
C4H5NO2; mol wt 99.09.
C 48.48%, H 5.09%, N 14.14%, O 32.29%.

Description and references

Prepd by rapid distillation of ammonium succinate: Clarke, Behr, Org. Synth. coll. vol. II (1943) p 562; Fehling, Ann. 49, 198 (1844); Bunge, Ann. Suppl. 7, 118 (1870); Menschutkin, Ann. 162, 166 (1872). Prepn by heating succinic acid with ammonia: Fehling, loc. cit.; Franchimont, Friedmann, Rec. Trav. Chim. 25, 79 (1906); with urea: Ma, Sah, C.A. 28, 6108 (1934); see also Tafel, Stern, Ber. 33, 2232 (1900); Koller, Ber. 37, 1598 (1904). Prevention of oxalic lithiasis in rats: J. M. Melon et al., Therapie 26, 991 (1971).

Chemical structure

Properties

Orthorhombic bipyramidal crystals from acetone or alc. mp 125-127°. d 1.41. bp 287-289° (slight decompn). pKa 9.5. One gram dissolves in 3 ml water, 0.7 ml boiling water, 24 ml alc, 5 ml alc at 60°. Insol in ether, chloroform. LD50 orally in rats: 14 g/kg (Melon).

Therapeutic Category

Antiurolithic.

Keywords

Antiurolithic