N-ethyl-N-(oxan-4-yl)carbamoyl chloride → N-ethyl-N-(tetrahydro-2H-pyran-4-yl)-4-(2-chlorophenyl)-4,5-dihydro-1H-tetrazol-5-one-1-carboxamide

HRID 650866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650866
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[N:11]=[N:10][NH:9]1.[CH2:14]([N:16]([CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:17](Cl)=[O:18])[CH3:15]>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH2:14]([N:16]([CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:17]([N:11]1[C:12](=[O:13])[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:9]=[N:10]1)=[O:18])[CH3:15]

Komponenten

5

Edukt 2

HCID 11127103N-ethyl-N-(oxan-4-yl)carbamoyl chlorideHCID 178518972HCID 178518972, Verbindung

Produkt 1

HCID 11013583N-ethyl-N-(tetrahydro-2H-pyran-4-yl)-4-(2-chlorophenyl)-4,5-dihydro-1H-tetrazol-5-one-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

3.7 g (19 mmol) of 1-(2-chlorophenyl)-1,2-dihydro-5H-tetrazol-5-one, 3.6 g (19 mmol) of N-ethyl-N-(tetrahydro-2H-pyran-4-yl)carbamoyl chloride and 2.6 g (21 mmol) of 4-dimethylaminopyridine in 150 ml of toluene were heated under reflux for 5 hours. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (eluent hexane/ethyl acetate 2:1). Yield 5.5 g. 1H NMR (270 MHz, in CDCl3): δ=1.20-1.40 (m, 3H), 1.80-2.05 (m, 4H), 3.30-3.60 (m, 4H), 3.70-4.50 (m, 3H), 7.40-7.60 (m, 4H).

Aufarbeitung

  1. temperatureunder reflux for 5 hours
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent hexane/ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-f4e2ad08a4a94f6a8acac5d84d95d13b
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06277790B1

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