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Acetic Acid → HCID 22929440, Verbindung

HRID 1828451
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1828451
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(O)(=O)C.CN(C)[CH:19]=[C:20]([C:26]1[N:27]=[N:28][N:29]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[N:30]=1)[C:21](OCC)=[O:22]>O>[CH3:39][O:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][N:29]2[N:28]=[N:27][C:26]([C:20]3[C:21](=[O:22])[N:12]4[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]4=[N:1][CH:19]=3)=[N:30]2)=[CH:33][CH:34]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 7015521Ethyl 2-aminopyridine-4-carboxylateHCID 53425728Ethyl 3-(dimethylamino)-2-{2-[(4-methoxyphenyl)methyl]-2H-tetrazol-5-yl}prop-2-enoate

Produkt 1

HCID 22929440HCID 22929440, VerbindungAusbeute 53,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Ethyl 2-aminoisonicotinate (6.5 g, 39.23 mmol) was added with acetic acid (500 ml) and ethyl 3-(dimethylamino)-2-[2-(4-methoxybenzyl)-2H-1,2,3,4-tetrazol-5-yl]-2-propenoate (13 g, 39.23 mmol) and refluxed by heating at 130° C. for 5 hours. The reaction solution was returned to room temperature and poured into water, and this was extracted with chloroform. The resulting organic layer was washed with saturated brine, and the collected organic layer was dried over magnesium sulfate. The organic layer was concentrated under reduced pressure and subjected to azeotropy with toluene, and the resulting residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=80:1→50:1→30:1) to obtain 8.6 g of the title compound.

Aufarbeitung

  1. temperaturerefluxed
  2. customwas returned to room temperature
  3. extractionthis was extracted with chloroform
  4. washThe resulting organic layer was washed with saturated brine
  5. dry with materialthe collected organic layer was dried over magnesium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=80:1→50:1→30:1)

Quellen und Nachweise

ORD-Eintrag
ord-321b0188985a407aacfd83a3b18cafbb
Quelldatensatz
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07056917B2

Notizen zur Reaktion

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