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Citric Acid → HCID 21266052, Verbindung

HRID 566316
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 566316
[NH:1]([CH:3]([CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:4])[NH2:2].C(N(CC)CC)C.[CH3:21][O:22][C:23](OC)=[C:24]([C:27]#[N:28])[C:25]#[N:26].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O>[NH2:28][C:27]1[N:1]([CH:3]([CH2:5][CH2:6][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH3:4])[N:2]=[C:23]([O:22][CH3:21])[C:24]=1[C:25]#[N:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 110079702-(dimethoxymethylidene)propanedinitrileHCID 12874625HCID 12874625, Verbindung

Produkt 1

HCID 21266052HCID 21266052, VerbindungAusbeute 80,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

3.6 g of 2-hydrazino-5-phenylpentane are dissolved in 40 ml of methanol, and 2.8 ml of triethylamine are added. Then, 2.8 g of 1,1-dimethoxy-2,2-dicyanoethylene are added at approx. 0° C. The reaction solution is warmed to approx. 20° C. and stirred for 1.5 hours at approx. 20° C. For work-up, the mixture is diluted with water, acidified with citric acid and extracted twice with dichloromethane. The combined dichloromethane phases are dried with magnesium sulphate and evaporated in vacuo. This gives 5.1 g of a yellow oil, which crystallizes slowly. The oil is chromatographed on silica gel (Merck Si 60 0.04-0.063 mm) with a petroleum ether/ethyl acetate mixture in a ratio of 5:1 to 1:1. This gives a fraction which, after evaporation in vacuo, affords 4.6 g (=80.9% of theory) of 5-amino-4-cyano-3-methoxy-1-[(5-phenyl)-pent-2-yl]-pyrazole.

Aufarbeitung

  1. extractionextracted twice with dichloromethane
  2. dry with materialThe combined dichloromethane phases are dried with magnesium sulphate
  3. customevaporated in vacuo
  4. customThis gives 5.1 g of a yellow oil, which crystallizes slowly
  5. customThe oil is chromatographed on silica gel (Merck Si 60 0.04-0.063 mm) with a petroleum ether/ethyl acetate mixture in a ratio of 5:1 to 1:1
  6. customThis gives a fraction which
  7. customafter evaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bbcced926d7b49a4a1ad03814ee79b9d
Quelldatensatz
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06174884B1

Notizen zur Reaktion

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