2-Chloroethanol → HCID 88465312, compound

A mixture of 4.9 g (0.035 mole) of 2-(3-pyridinyloxy)ethanol[prepared as an oil by procedure of Preparation 21 from 14 g (0.15 mole) of 3-hydroxypyridine, 27 ml (0.40 mole) of 2-chloroethanol and 85 g of potassium carbonate] and 8 g (0.046 mole) of sulfamic acid phenyl ester in 100 ml of dioxane was heated at reflux temperatue for 20 min and the solvent then evaporated. The residue was triturated with 250 ml of acetone, filtered, and the filtrate acidified with a solution of anhydrous hydrogen chloride in isopropyl alcohol and the sticky, brown precipitate collected. The brown solid was redissolved in 125 ml of methanol and diluted with 125 ml of ethanol. The solution was stirred with charcoal, filtered, and the filtrate partially evaporated to give a suspension. The suspension was diluted with isopropyl alcohol-isopropyl ether and filtered. The solid was dried at 50° C. for 18 hr and then at 70° C. for 18 hr in a vacuum oven. The yield was 4.5 g of solid, mp 156°-157° C.

1. temperaturewas heated
2. temperatureat reflux temperatue for 20 min
3. customthe solvent then evaporated
4. customThe residue was triturated with 250 ml of acetone
5. filtrationfiltered
6. customthe sticky, brown precipitate collected
7. dissolutionThe brown solid was redissolved in 125 ml of methanol
8. additiondiluted with 125 ml of ethanol
9. filtrationfiltered
10. customthe filtrate partially evaporated
11. customto give a suspension
12. filtrationfiltered
13. customThe solid was dried at 50° C. for 18 hr

ORD record

ord-4c8fc09c1b5e45bfa7bd54b3d972bc3a

Source dataset

uspto-grants-1991_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05025031