Glycol monoethyl ether → 2,2-Dichloro-N-[(2-ethoxyethoxy)methyl]-N-propylacetamide

A solution containing N-propyl-N-chloromethyldichloroacetamide (21.9 g., 0.1 mole) and 2-ethoxyethanol (30 ml.) is weighed in a flask equipped as in Example 1. A solution prepared from metallic sodium (2.3 g., 0.1 mole) with ethoxyethanol (20 ml.) is added to the solution under stirring and cooling by water in such a rate that the temperature of the mixture is maintained below 35° C. After the addition is complete, the mixture is stirred for an additional 2 hours at room temperature. Then, the bulk of ethoxyethanol is removed under reduced pressure and the residue is dissolved in chloroform (80 ml.). The chloroform solution is washed with water (2×100 ml.), dried over anhydrous sodium sulfate and the solvent is distilled under reduced pressure to give 23.2 g. (90.0%) of the named product as an oil; nD25 =1.4651.

1. customis weighed in a flask
2. customequipped as in Example 1
3. additionis added to the solution
4. temperatureis maintained below 35° C
5. additionAfter the addition
6. stirringthe mixture is stirred for an additional 2 hours at room temperature
7. customThen, the bulk of ethoxyethanol is removed under reduced pressure
8. dissolutionthe residue is dissolved in chloroform (80 ml.)
9. washThe chloroform solution is washed with water (2×100 ml.)
10. dry with materialdried over anhydrous sodium sulfate
11. distillationthe solvent is distilled under reduced pressure
12. customto give 23.2 g

ORD record

ord-2ae8d217ae014ffd85756a61cafb0e75

Source dataset

uspto-grants-1989_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04843177