Triethylamine → HCID 25102948, Verbindung

HRID 238558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238558
[O:1]1[CH2:6][CH2:5][CH:4]=[CH:3][C:2]1=[O:7].[CH2:8]([N:10](CC)CC)C.[N:15]1[O:16][N:17]=[C:18]2[CH:23]=[C:22]([C:24](Cl)=[O:25])[CH:21]=[CH:20][C:19]=12>CN.C(O)C.ClCCl>[CH3:8][N:10]([CH:4]1[CH2:5][CH2:6][O:1][C:2](=[O:7])[CH2:3]1)[C:24]([C:22]1[CH:21]=[CH:20][C:19]2=[N:15][O:16][N:17]=[C:18]2[CH:23]=1)=[O:25]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 5206605,6-Dihydro-2H-pyran-2-oneHCID 27354532,1,3-Benzoxadiazole-5-carbonyl chloride

Produkt 1

HCID 25102948HCID 25102948, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6329MethylamineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

5,6-Dihydro-2H-pyran-2-one (1.0 g, 10.2 mmol) was dissolved in 3 ml of a 33% solution of methylamine in ethanol and heated to 55° C. overnight. The solvent was evaporated, the residue dissolved in methanol (20 ml) and conc. HCl (20 ml) and the mixture heated at 95° C. for 2.5 h. The mixture was evaporated to dryness, the residue dissolved in THF (20 ml), dichloromethane (20 ml) and triethylamine (3 ml) and a solution of [2,1,3]-benzoxadiazole-5-carboxylic acid chloride (2.0 g, 11 mmol), in dichloromethane (5 ml), added. After stirring the mixture for 0.75 h, the mixture was washed with 1N HCl and conc. NaHCO3 solution, dried over sodium sulfate, and concentrated under vacuum. The residue was purified on a silica gel column using ethyl acetate/hexane/dichloromethane (70:20:10), to give N-methyl-N-(2-oxotetrahydro-2H-pyran-4-yl)-[2,1,3]-benzoxadiazole-5-carboxamide as white solid after crystallization from dichloromethane/methanol (0.21 g). Mp=169-171° C., 1H NMR (300 MHz, CDCl3, rotamers) δ 7.97 (d, J=9.0 Hz, 1H); 7.90 (s, 1H); 7.40 (d, J=9.0 Hz, 1H); 5.10-4.40 (m, 3H); 3.01 (s, 3H); 3.00-2.74 (m, 2H) and 2.60-2.10 ppm (s, 2H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in methanol (20 ml)
  3. temperatureconc. HCl (20 ml) and the mixture heated at 95° C. for 2.5 h
  4. customThe mixture was evaporated to dryness
  5. dissolutionthe residue dissolved in THF (20 ml)
  6. washthe mixture was washed with 1N HCl and conc. NaHCO3 solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-6c91c108bd304162af4765ea8c8e70f4
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642633B2

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