Reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([Cl:11])([Cl:10])[Cl:9])[CH:5]=[C:4]([Cl:12])[N:3]=1.[Na].[CH3:14][O:15][CH2:16][CH2:17][OH:18]>>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([Cl:11])([Cl:10])[Cl:9])[CH:7]=[C:2]([O:18][CH2:17][CH2:16][O:15][CH3:14])[N:3]=1Participants
Procedure
To a solution of 26.54 grams (0.10 mole) of 2,6-dichloro-4-(trichloromethyl)pyridine dissolved in 150 milliliters (ml) of 2-methoxyethanol was added over a 35 minute period, a solution composed of 2.53 grams (0.11 mole) of sodium metal dissolved in 100 ml of 2-methoxyethanol. The mixture was stirred for 5 hours at 65°-75° C. The insoluble by-products were removed by filtration and the 2-methoxyethanol was removed by evaporation under reduced pressure. The resulting oily product was diluted with water and extracted with methylene chloride and dried with sodium sulfate. The methylene chloride was then removed leaving the 2-chloro-6-(2-methoxyethoxy)-4-(trichloromethyl)pyridine as an oil. The product was recovered in a yield of 25.6 grams (84 percent of theoretical) and had a refractive index of n 25/d = 1.5440. Upon analysis, the compound was found to have carbon, hydrogen and nitrogen contents of 35.48, 2.99 and 4.72 percent, respectively, as compared with the theoretical contents of 35.44, 2.97 and 4.59 percent, respectively, as calculated for the above named structure.
Workup
- additionwas added over a 35 minute period
- customThe insoluble by-products were removed by filtration
- customthe 2-methoxyethanol was removed by evaporation under reduced pressure
- additionThe resulting oily product was diluted with water
- extractionextracted with methylene chloride
- dry with materialdried with sodium sulfate
- customThe methylene chloride was then removed
Sources & evidence
- ORD record
- ord-b0b65b64916149bea499c561a78da65e
- Source dataset
- uspto-grants-1979_03
- Patent number
- US04143144
Linked notes
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