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5-methyl-1H-pyrazole-3-carboxylic acid → HCID 53972348, Verbindung

HRID 1763936
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1763936
ClC(OCC)=O.[CH3:7][C:8]1[NH:12][N:11]=[C:10]([C:13]([OH:15])=O)[CH:9]=1.Cl.[NH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=1.[OH-].[Na+]>C(O)C.C(N(CC)CC)C.O1CCCC1>[CH3:7][C:8]1[NH:12][N:11]=[C:10]([C:13]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:22][CH:21]=2)=[O:15])[CH:9]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 98225-methyl-1H-pyrazole-3-carboxylic acidHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 20463439Ethyl 3-[4-(2-aminoethyl)phenyl]propanoate--hydrogen chloride (1/1)

Produkt 1

HCID 53972348HCID 53972348, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702
Ethanol
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

1.27 ml. triethylamine and 0.85 ml. ethyl chloroformate are added at -10° C. to a solution of 1.12 g. of 5-methylpyrazole-3-carboxylic acid in 25 ml. anhydrous tetrahydrofuran. After 15 minutes, a further 1.27 ml. triethylamine is added and then 2.57 g. ethyl β-[4-(2-aminoethyl)-phenyl]-propionate hydrochloride. The reaction mixture is stirred for 1 hour at +20° C., filtered with suction and the filtrate is evaporated and the residue taken up in methylene chloride. After extraction with 2N hydrochloric acid, 2N aqueous sodium hydroxide solution and neutralization, the solution is dried and evaporated. The crude ester thus obtained is heated under reflux for 1 hour with 0.6 g. sodium hydroxide in 30 ml. ethanol. After cooling, the precipitated sodium salt is filtered off with suction, dissolved in water and carefully acidified. The precipitate obtained is filtered off and recrystallized from 20% ethanol. There is obtained β-{4-[2-(5-methylpyrazole- 3-carboxamido)-ethyl]-phenyl}-propionic acid in a yield of 22% of theory; m.p. 202°-205° C.

Aufarbeitung

  1. filtrationfiltered with suction
  2. customthe filtrate is evaporated
  3. extractionAfter extraction with 2N hydrochloric acid, 2N aqueous sodium hydroxide solution and neutralization
  4. customthe solution is dried
  5. customevaporated
  6. customThe crude ester thus obtained
  7. temperatureis heated
  8. temperatureunder reflux for 1 hour with 0.6 g
  9. temperatureAfter cooling
  10. filtrationthe precipitated sodium salt is filtered off with suction
  11. dissolutiondissolved in water
  12. customThe precipitate obtained
  13. filtrationis filtered off
  14. customrecrystallized from 20% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-116d710299ad415ea1bfed0e46dd2a20
Quelldatensatz
uspto-grants-1978_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04113871

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