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Carbon tetrabromide → ethyl 1-({5-[3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl}methyl)-1H-pyrazole-4-carboxylate

HRID 1257423
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Reaktionsgleichung

Reaktionsgleichung von HRID 1257423
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]([OH:14])=O)[CH:10]=1)=[O:5])[CH3:2].Cl.[F:16][C:17]([F:29])([F:28])[C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([NH:23][NH2:24])=O.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:16][C:17]([F:28])([F:29])[C:18]1[CH:19]=[C:20]([C:21]2[O:14][C:12]([CH2:11][N:9]3[CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=[N:8]3)=[N:24][N:23]=2)[CH:25]=[CH:26][CH:27]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 59557975[4-(ethoxycarbonyl)-1H-pyrazol-1-yl]acetic acidHCID 669395863-(Trifluoromethyl)benzohydrazide hydrochloride

Produkt 1

HCID 58127966ethyl 1-({5-[3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl}methyl)-1H-pyrazole-4-carboxylateAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of the compound (1.0 g) obtained in Example 115b in dichloromethane (15 ml) was cooled in an ice bath, N,N′-carbonyldiimidazole (0.81 g) was added and the mixture was stirred for 30 min. 3-(Trifluoromethyl)benzohydrazide hydrochloride (1.2 g) was added, and the mixture was stirred at the same temperature for 45 min. Then, carbon tetrabromide (3.32 g) and triphenylphosphine (2.6 g) were added, and the mixture was further stirred at the same temperature for 2 hr. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (carrier: silica gel, eluent: petroleum ether-ethyl acetate) to give the title compound (0.64 g) as a colorless oil.

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 45 min
  2. stirringthe mixture was further stirred at the same temperature for 2 hr
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by column chromatography (carrier: silica gel, eluent: petroleum ether-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-85aff709d24a4076868f36e0b13b050f
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08461348B2

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