Triethylamine → Ethyl 1-(2-fluorobenzyl)-1H-imidazo[2,1-c][1,2,4]triazole-3-carboxylate

HRID 1640337Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640337
Cl/[C:2](=[N:8]\[NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])/[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(S[C:22]1[NH:23][CH:24]=[CH:25][N:26]=1)C=C.C(N(CC)CC)C>O1CCOCC1>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][N:9]1[C:22]2=[N:26][CH:25]=[CH:24][N:23]2[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:8]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 552877472-Allylsulfanyl-1H-imidazoleHCID 58142732ethyl (2Z)-2-chloro-2-[(2-fluorophenyl)methylhydrazinylidene]acetate

Produkt 1

HCID 58142731Ethyl 1-(2-fluorobenzyl)-1H-imidazo[2,1-c][1,2,4]triazole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Ethyl (2Z)-chloro[(2-fluorobenzyl)hydrazono]acetate (750 mg, 2.90 mmol) from example 2A, 2-allylthio-1H-imidazole [U.S. Pat. No. 3,574,593; Chem. Abstr. 75, 49078] (1.20 g, 7.25 mmol) and triethylamine (293 mg, 2.90 mmol) are dissolved in dioxane (10 ml) and heated under reflux for 4 h. This is followed by dilution with water and extraction with ethyl acetate. The organic phase is dried over sodium sulfate, and the crude product is purified by chromatography on silica gel (eluent: dichloromethane/methanol 50:1). 410 mg (41% of theory) of the desired product are obtained with 84% purity.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 4 h
  3. extractionThis is followed by dilution with water and extraction with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe crude product is purified by chromatography on silica gel (eluent: dichloromethane/methanol 50:1)

Quellen und Nachweise

ORD-Eintrag
ord-88ef207e309d442ca261c1b95463e627
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114400B2

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