3-Pyridinecarbonyl chloride, hydrochloride (1:1) → 2,2,7,7-Tetramethyloctane-1,8-diyl dipyridine-3-carboxylate

HRID 1262822노트

반응식

HRID 1262822 반응식
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[CH3:11][C:12]([CH3:24])([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:23])([CH3:22])[CH2:20][OH:21])[CH2:13][OH:14]>N1C=CC=CC=1>[C:2]([O:21][CH2:20][C:19]([CH3:23])([CH3:22])[CH2:18][CH2:17][CH2:16][CH2:15][C:12]([CH3:24])([CH3:11])[CH2:13][O:14][C:2](=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1

참가 물질

4

반응물 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 2138481,8-Octanediol, 2,2,7,7-tetramethyl-

생성물 1

HCID 30696732,2,7,7-Tetramethyloctane-1,8-diyl dipyridine-3-carboxylate수율 53.4%

시약·촉매·용매 1

HCID 1049Pyridine용매2회

실험 절차

A suspension of 106.2 grams (0.6 mole) of nicotinoyl chloride hydrochloride in 300 ml of anhydrous pyridine was added in 2 hours under stirring with a solution of 20.2 grams (0.1 mole) of 2,2,7,7-tetramethyl-1,8-octanediol in 60 ml of anhydrous pyridine while keeping the temperature at about 70° C. The reaction was refluxed and stirred for 36 hours, then, after cooling, the formed precipitate was removed by filtration. The filtrate was evaporated under vacuum and the obtained residue was treated with a mixture of 200 ml of diethyl ether and 100 ml of an 8% aqueous solution of sodium bicarbonate. The organic layer was separated, washed first with 100 ml of a 3% aqueous solution of sodium bicarbonate, then with 100 ml of water and finally concentrated under vacuum to about half of the initial volume. After standing overnight, the product which separated was recovered by filtration and recrystallized from ethanol thus obtaining 22 grams of the title product, having m.p. 89° -90° C. Yield 53.4% of theoretical.

후처리

  1. additionwas added in 2 hours
  2. customat about 70° C
  3. temperatureThe reaction was refluxed
  4. temperatureafter cooling
  5. customthe formed precipitate was removed by filtration
  6. customThe filtrate was evaporated under vacuum
  7. additionthe obtained residue was treated with a mixture of 200 ml of diethyl ether and 100 ml of an 8% aqueous solution of sodium bicarbonate
  8. customThe organic layer was separated
  9. washwashed first with 100 ml of a 3% aqueous solution of sodium bicarbonate
  10. concentrationwith 100 ml of water and finally concentrated under vacuum to about half of the initial volume
  11. waitAfter standing overnight
  12. customthe product which separated
  13. filtrationwas recovered by filtration
  14. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-7e236bd1e8e147b09e3e9cfe8cfb18e6
출처 데이터셋
uspto-grants-1984_06
특허 번호
US04454145

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