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Triethylamine → 4-(2,4-Dimethoxyphenyl)pyridine-2,6-dicarboxylic Acid

HRID 5553
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 5553
BrCC1C=C(CBr)C=C(CBr)C=1.CCN(CC)CC.C[O:21][C:22]([C:24]1[CH:29]=[C:28]([C:30]2[CH:35]=[C:34](S(Cl)(=O)=O)[C:33]([O:40][CH3:41])=[CH:32][C:31]=2[O:42][CH3:43])[CH:27]=[C:26]([C:44]([O:46]C)=[O:45])[N:25]=1)=[O:23].C(NCCO)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl.CO.C(Cl)(Cl)Cl.O>[CH3:43][O:42][C:31]1[CH:32]=[C:33]([O:40][CH3:41])[CH:34]=[CH:35][C:30]=1[C:28]1[CH:27]=[C:26]([C:44]([OH:46])=[O:45])[N:25]=[C:24]([C:22]([OH:23])=[O:21])[CH:29]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 5302581,3,5-Tris(bromomethyl)benzene2×HCID 31256082-((Triphenylmethyl)amino)ethanolHCID 150019164-(5-Chlorosulfonyl-2,4-dimethoxyphenyl)-2,6-pyridine dicarboxylic acid dimethyl ester

Produkt 1

HCID 150019144-(2,4-Dimethoxyphenyl)pyridine-2,6-dicarboxylic Acid

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 21584188Chloroform methanolLösungsmittel

Versuchsvorschrift

To a suspension of 0.5 g (0.0008 mole) of the amine-hydrochloride 8 in 20 ml of CH2Cl2 was added all at once 1.4 ml (0.01 mole) of Et3N. The mixture was then cooled to 5°-10° C. and 1.4 g (0.0032 mole) of the sulfonyl chloride 39 in 20 ml of CH2Cl2 was slowly added in a dropwise fashion. The reaction was then allowed to stir at room temperature for 30 minutes after which a TLC was taken. Little of the sulfonyl chloride 9 had reacted by TLC so an additional 100 mg of the amine 8 was added and stirring continued overnight. The mixture was then poured into water and extracted with CH2Cl2. The extract was washed with water, dried (Na2SO4) and the solvent removed yielding crude 43. After column chromatography with SiO2 /5%MeOH/CHCl3, 1.55 g (93%) of the desired tetraamide 43 was obtained.

Aufarbeitung

  1. temperatureThe mixture was then cooled to 5°-10° C.
  2. additionwas added
  3. stirringstirring continued overnight
  4. extractionextracted with CH2Cl2
  5. washThe extract was washed with water
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed
  8. customyielding crude 43

Quellen und Nachweise

ORD-Eintrag
ord-1c4af60950e34e5ba3caea2d9484da0b
Quelldatensatz
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05245038

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