US 11,986,779 B2
Recrystallized HI-6 dimethylsulfate
Shawn T. Blumberg, San Antonio, TX (US); and Paul W. Miguel, San Antonio, TX (US)
Assigned to SOUTHWEST RESEARCH INSTITUTE, San Antonio, TX (US)
Filed by Southwest Research Institute, San Antonio, TX (US)
Filed on Nov. 10, 2020, as Appl. No. 16/949,666.
Claims priority of provisional application 62/933,814, filed on Nov. 11, 2019.
Prior Publication US 2021/0138359 A1, May 13, 2021
Int. Cl. B01D 9/00 (2006.01); C07C 309/04 (2006.01); C07D 213/81 (2006.01)
CPC B01D 9/0054 (2013.01) [C07C 309/04 (2013.01); C07D 213/81 (2013.01)] 5 Claims
 
1. A method for making a solvate and hydrate of (1-(2-(hydroxyiminomethyl)pyridinium)-3-(4-carbamoylpyridinium)-2-oxapropane) dimethanesulfonate comprising:
dissolving (1-(2-(hydroxyiminomethyl)pyridinium)-3-(4-carbamoylpyridinium)-2-oxapropane) dimethanesulfonate in an alkyl-based glycol comprising ethylene glycol or 1,2-propane diol and adding an antisolvent comprising tert-butanol to make a solvate and hydrate of (1-(2-(hydroxyiminomethyl)pyridinium)-3-(4-carbamoylpyridinium-2-oxapropane) dimethanesulfonate wherein said solvate and hydrate of (1-(2-(hydroxyiminomethyl)pyridinium)-3-(4-carbamoylpyridinium)-2-oxapropane) does not absorb water over a seven-day period under ambient temperature and humidity conditions.