Potassium Carbonate → N-(2,3-Dihydroxypropyl)-2-methylprop-2-enamide

Temperature

0 °C

4.65 g of 3-amino-1,2-propanediol (0.05 mol) were dissolved in 30 ml of dimethylformamide (anhydrous). This solution and 13.8 g of K2CO3 were placed in a 100 ml three-necked flask with dropping funnel and gas inlet and gas outlet tubes. The mixture was cooled to 0° C. in an ice bath. While stirring gently and slowly bubbling nitrogen through, 6.18 ml of methacryloyl chloride (0.06 mol) dissolved in 30 ml of dimethylformamide were added dropwise over the course of 30 minutes. The mixture was stirred, while cooling in ice, for a further hour and then allowed to warm to room temperature and was stirred for a further 30 minutes. The reaction mixture was filtered through a fluted filter, and the residue was discarded. The filtrate was concentrated to a viscous oil in a rotary evaporator. This oil was dissolved in 30 ml of methanol, a second filtration was carried out, and the filtrate was again concentrated in a rotary evaporator. The residues of the solvent were removed under high vacuum. The yield was 8.52 g.

1. additionwere added dropwise over the course of 30 minutes
2. stirringThe mixture was stirred
3. temperaturewhile cooling in ice, for a further hour
4. temperatureto warm to room temperature
5. stirringwas stirred for a further 30 minutes
6. filtrationThe reaction mixture was filtered through
7. filtrationa fluted filter
8. concentrationThe filtrate was concentrated to a viscous oil in a rotary evaporator
9. dissolutionThis oil was dissolved in 30 ml of methanol
10. filtrationa second filtration
11. concentrationthe filtrate was again concentrated in a rotary evaporator
12. customThe residues of the solvent were removed under high vacuum

ORD record

ord-4d1acf79a9eb40ab9af9d80a3843bfb1

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05232859