Dimethylformamide → HCID 178496176, Verbindung

HRID 1661960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1661960
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:19])=[C:8]([CH:12]=[CH:13][C:14]=1[S:15]([CH3:18])(=[O:17])=[O:16])[C:9]([OH:11])=O.C(Cl)(=O)C(Cl)=O.CN(C=O)C.Cl.[OH:32][C:33]1[N:37]([CH3:38])[N:36]=[CH:35][CH:34]=1>C(Cl)(Cl)Cl.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:19])=[C:8]([C:9]([C:34]2[CH:35]=[N:36][N:37]([CH3:38])[C:33]=2[OH:32])=[O:11])[CH:12]=[CH:13][C:14]=1[S:15]([CH3:18])(=[O:17])=[O:16]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 667565243-(2-Methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acidHCID 178478934HCID 178478934, Verbindung

Produkt 1

HCID 178496176HCID 178496176, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6212ChloroformLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid (195 mg, 6.76 mmol) in chloroform (15 mL) were added oxalyl-chloride (0.5 mL) and DMF in a catalytic amount. The reaction mixture was stirred for 30 minutes at room temperature, and the solvent was distilled off under reduced pressure. The residue was dissolved in anhydrous THF (20 mL), and 5-hydroxy-1-methylpyrazole hydrochloride (136 mg, 1.01 mmol), triethylamine (136 mg) and N,N-dimethylaminopyridine (250 mg) were added, followed by reflux with heating for 1 hour. The reaction mixture was allowed to cool to room temperature, and diluted with ethyl acetate (200 mL). The mixture was washed twice with a saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in anhydrous acetonitrile (10 mL), and triethylamine (136 mg) and acetone cyanohydrin in a catalytic amount were added. The mixture was stirred for 12 hours at room temperature. The solvent was distilled off under reduced pressure to obtain crude 5-hydroxy-1-methylpyrazol-4-yl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone.

Aufarbeitung

  1. distillationthe solvent was distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in anhydrous THF (20 mL)
  3. temperatureby reflux
  4. temperaturewith heating for 1 hour
  5. temperatureto cool to room temperature
  6. washThe mixture was washed twice with a saturated brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. dissolutionThe residue was dissolved in anhydrous acetonitrile (10 mL)
  10. additiontriethylamine (136 mg) and acetone cyanohydrin in a catalytic amount were added
  11. stirringThe mixture was stirred for 12 hours at room temperature
  12. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a50378f878e646869b695393d262107a
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030498B2

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