Sulfuric Acid → 2-Ethylhexyl 4-amino-3,6-dichloropyridine-2-carboxylate

HRID 378774

반응식

HRID 378774 반응식
[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][OH:5])[CH3:2].S(=O)(=O)(O)O.[NH2:15][C:16]1[CH:21]=[C:20]([Cl:22])[N:19]=[C:18]([C:23](O)=[O:24])[C:17]=1[Cl:26]>O>[NH2:15][C:16]1[CH:21]=[C:20]([Cl:22])[N:19]=[C:18]([C:23]([O:5][CH2:4][CH:3]([CH2:1][CH3:2])[CH2:6][CH2:7][CH2:8][CH3:9])=[O:24])[C:17]=1[Cl:26]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 77202-EthylhexanolHCID 213012Aminopyralid

생성물 1

HCID 216966212-Ethylhexyl 4-amino-3,6-dichloropyridine-2-carboxylate

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 2-ethylhexanol (10 mL) and sulfuric acid (1 mL) was added 4-amino-3,6-dichloro-pyridine-2-carboxylic acid (0.0097 mol, 2.0 g). After heating the reaction to reflux overnight, the reaction mixture was cooled, poured into water (75 mL), and extracted with ethyl acetate (75 mL). The organic phase was washed with sodium bicarbonate (75 mL), dried (Na2SO4), and concentrated. The resulting solid was recrystallized out of dichloromethane and hexane and filtered to give 2-ethylhexyl 4-amino-3,6-dichloropyridine-2-carboxylate (0.0074 mol, 2.36 g) as a crystalline solid (mp 55° C.). 1H NMR (CDCl3): δ 0.9 (7 H, m), 1.3 (7 H, m), 1.7 (1 H, m), 4.3 (2 H, d), 5.1 (2 H, bs), 6.7 (1 H, s).

후처리

  1. temperatureAfter heating
  2. customthe reaction
  3. temperatureto reflux overnight
  4. temperaturethe reaction mixture was cooled
  5. extractionextracted with ethyl acetate (75 mL)
  6. washThe organic phase was washed with sodium bicarbonate (75 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe resulting solid was recrystallized out of dichloromethane and hexane
  10. filtrationfiltered

출처 및 근거

ORD 기록
ord-01f78302bb844d9c899e5af333717ca4
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297197B1

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