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Sodium Carbonate → 5-(cyclopropylmethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylic acid

HRID 1717291
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1717291
[CH:1]1([CH2:4][C:5](=O)[CH2:6][C:7]([O:9]CC)=[O:8])[CH2:3][CH2:2]1.[N:13]([C:16]1[CH:26]=[CH:25][C:19]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1)=[N+:14]=[N-:15].[O-]CC.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH:1]1([CH2:4][C:5]2[N:13]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=3)[N:14]=[N:15][C:6]=2[C:7]([OH:9])=[O:8])[CH2:2][CH2:3]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 2723922Sodium ethoxideHCID 21099281Ethyl 4-cyclopropyl-3-oxobutanoateHCID 594322264-azido-N-ethylbenzamide

Produkt 1

HCID 685122045-(cyclopropylmethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylic acidAusbeute 101,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Ethyl 4-cyclopropyl-3-oxobutyrate (1.20 g, 7.05 mmol, 1.2 eq.) obtained in Example 96a) and 4-azido-N-ethylbenzamide (1.20 g, 5.88 mmol) were dissolved in ethanol (25 ml), sodium ethoxide (556 mg, 7.35 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 30 min and at 80° C. for 2.5 hr. 2% Aqueous sodium carbonate solution (40 ml) was added to the reaction mixture, ethanol was evaporated, and the residue was diluted with water (20 ml) and washed twice with ethyl acetate-hexane (2:1, 50 ml). The organic layer was extracted with 1% aqueous sodium carbonate solution (20 ml). The aqueous layers were combined, acidified (pH<3) with 6N hydrochloric acid, and stood still at 5° C. The precipitate was collected by filtration, washed with cold water and dried to give the title compound as a pale-brown powder (1.88 g, 5.98 mmol, 101.7%).

Aufarbeitung

  1. customwas evaporated
  2. additionthe residue was diluted with water (20 ml)
  3. washwashed twice with ethyl acetate-hexane (2:1, 50 ml)
  4. extractionThe organic layer was extracted with 1% aqueous sodium carbonate solution (20 ml)
  5. customstood still at 5° C
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with cold water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-48dcebec2fa6453fa2e17c2eff64d7a1
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07803822B2

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