Ethylamine → 3-(ethylamino)-2-hydroxy-1-propanesulfonic acid

Temperature

4.699999809265137 °C

A solution of 3-chloro-2-hydroxy-1-propanesulfonic acid sodium salt (10 g, 50.9 mmol) in water (total volume: 40 mL) was added over 5 hours, via a syringe pump, to a cold (4.7° C.) solution of ethyl amine in water. The mixture was stirred for an additional 2 hours at 4.7° C. then for 18 hours at room temperature. NMR: quantitative yield. The mixture was concentrated. A solid could not be obtained: the sodium salt was too hygroscopic. The solution was treated with Amberlite IR-120 Plus, acid form, ion-exchange resin to give the free acid. It was still too hygroscopic to be obtained as a solid form. Submitted as a solution: d=1.314 g/mL, 62.5% w/w of the free acid in water. The 1H and 13C NMR and MS were consistent with the structure.

1. waitfor 18 hours at room temperature
2. concentrationThe mixture was concentrated
3. customA solid could not be obtained
4. additionThe solution was treated with Amberlite IR-120 Plus, acid form, ion-exchange resin
5. customto give the free acid
6. customto be obtained as a solid form

ORD record

ord-36d493ff747b4a87872239fe8b50d06d

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642801B2