Tetrahydrofuran → 1-(4-fluoro-2-methylaminophenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone

HRID 542798

Reaktionsgleichung

Reaktionsgleichung von HRID 542798
C([Li])CCC.[CH3:6][N:7]1[C:11]([CH3:12])=[N:10][N:9]=[N:8]1.O1CCCC1.[F:18][C:19]1[CH:28]=[CH:27][C:22]([C:23](OC)=[O:24])=[C:21]([NH:29][CH3:30])[CH:20]=1>CCCCCC.O>[F:18][C:19]1[CH:28]=[CH:27][C:22]([C:23](=[O:24])[CH2:12][C:11]2[N:7]([CH3:6])[N:8]=[N:9][N:10]=2)=[C:21]([NH:29][CH3:30])[CH:20]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 788251,5-DimethyltetrazoleHCID 13474393Methyl 4-fluoro-2-(methylamino)benzoateHCID 178418339Butyllithium

Produkt 1

HCID 134743941-(4-fluoro-2-methylaminophenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of butyl lithium in hexane (50 ml of 1.6M solution) was added slowly to a stirred mixture of 1,5-dimethyltetrazole (7.84 g) and dry tetrahydrofuran (170 ml) at 0°-5° under nitrogen. The mixture was stirred at 0°-5° for 0.5 hour and then methyl 4-fluoro-2-methylaminobenzoate (4.84 g) was added in portions at 0°-5°. The mixture was stirred at room temperature for 3 hours and then poured into water (500 ml). The resulting mixture was extracted with dichloromethane (5×60 ml). The extract was dried and evaporated to give an oil which partially solidified overnight. The solid was collected by filtration, washed with toluene and dried in vacuo to give the novel compound 1-(4-fluoro-2-methylaminophenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone, m.p. 132°-134°.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. extractionThe resulting mixture was extracted with dichloromethane (5×60 ml)
  3. customThe extract was dried
  4. customevaporated
  5. customto give an oil which partially solidified overnight
  6. filtrationThe solid was collected by filtration
  7. washwashed with toluene
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7340d66b0e6e414fb721ae3a56ac4fc4
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659718

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