Triethylamine → 1-(3-Bromo-phenyl)-3,5-diethyl-1H-pyrazole-4-carboxylic acid methyl ester

HRID 1011863

Reaktionsgleichung

Reaktionsgleichung von HRID 1011863
[CH3:1][O:2][C:3](=[O:14])[C:4]([C:10](=O)[CH2:11][CH3:12])=[C:5](OC)[CH2:6][CH3:7].Cl.[Br:16][C:17]1[CH:18]=[C:19]([NH:23][NH2:24])[CH:20]=[CH:21][CH:22]=1.CCN(CC)CC>CO>[CH3:1][O:2][C:3]([C:4]1[C:10]([CH2:11][CH3:12])=[N:24][N:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([Br:16])[CH:18]=2)[C:5]=1[CH2:6][CH3:7])=[O:14]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 337573-Bromophenylhydrazine hydrochlorideHCID 866265863-Methoxy-2-propionyl-pent-2-enoic acid methyl ester

Produkt 1

HCID 673139921-(3-Bromo-phenyl)-3,5-diethyl-1H-pyrazole-4-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel3×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A solution of 7.10 g (35.5 mmol) of (E and/or Z)-3-methoxy-2-propionyl-pent-2-enoic acid methyl ester in 10 ml of MeOH was added to a solution of 8.09 g (35.5 mmol) of 3-bromophenylhydrazine hydrochloride in 150 ml of MeOH and the mixture was cooled to −20° C. To this mixture was added a solution of 3.79 g=5.22 ml (37.2 mmol) of Et3N in 40 ml of MeOH drop by drop and the reaction was then warmed up to RT. After 20 hours, it was poured into crashed ice and extracted twice with Et2O; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated to give 7.62 g of the title compound as light red oil. MS: 337.1 (MH+, 1 Br).

Aufarbeitung

  1. temperaturethe reaction was then warmed up to RT
  2. additionit was poured
  3. extractionextracted twice with Et2O
  4. washthe organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2ef6c5d1a79e480ea21fcd46cbeef319
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977358B2

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