Glycol monoethyl ether → 2-Chloro-6-(2-ethoxyethoxy)-4-(trichloromethyl)pyridine

HRID 614078

反応式

HRID 614078 の反応式
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].[CH2:14]([O:16][CH2:17][CH2:18][OH:19])[CH3:15]>>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([Cl:11])([Cl:10])[Cl:9])[CH:7]=[C:2]([O:19][CH2:18][CH2:17][O:16][CH2:14][CH3:15])[N:3]=1

参加物

4

反応物 3

HCID 8076Glycol monoethyl ether2 回HCID 897822,6-Dichloro-4-(trichloromethyl)pyridineHCID 5360545Sodium

生成物 1

HCID 213300072-Chloro-6-(2-ethoxyethoxy)-4-(trichloromethyl)pyridine

実験手順

To a solution of 26.54 grams (0.1 mole) of 2,6-dichloro-4-(trichloromethyl)pyridine dissolved in 150 ml of 2-ethoxyethanol was added over a 35 minute period, a solution of 2.53 grams (0.11 mole) of sodium metal dissolved in ~100 ml of 2-ethoxyethanol. The mixture was heated for 5 hours at 65°-75° C. The insoluble by-products were filtered off and the 2-ethoxyethanol was removed by evaporation under reduced pressure. The residue which remained was diluted with water and extracted with methylene chloride and the extract dried with sodium sulfate. The extract was filtered and the methylene chloride evaporated off leaving the 2-chloro-6-(2-ethoxyethoxy)-4-(trichloromethyl)pyridine product as an oil. The product had a refractive index of n 25/d = 1.5395 and was recovered in a yield of 23.8 grams (75 percent of theoretical). Upon analysis, the compound was found to have carbon, hydrogen, nitrogen and chlorine contents of 37.72, 3.25, 4.55 and 44.61 percent, respectively, as compared with the theoretical contents of 37.64, 3.48, 4.39 and 44.45 percent, respectively, as calculated for the above named compound.

後処理

  1. additionwas added over a 35 minute period
  2. temperatureThe mixture was heated for 5 hours at 65°-75° C
  3. filtrationThe insoluble by-products were filtered off
  4. customthe 2-ethoxyethanol was removed by evaporation under reduced pressure
  5. additionThe residue which remained was diluted with water
  6. extractionextracted with methylene chloride
  7. dry with materialthe extract dried with sodium sulfate
  8. filtrationThe extract was filtered
  9. customthe methylene chloride evaporated off

出典と根拠

ORDレコード
ord-1251f4c1ae9b452a8134886940a26a7b
出典データセット
uspto-grants-1979_03
特許番号
US04143144

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