Potassium Carbonate → 5-(3-Fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)-2,3-dimethyl-benzamide

HRID 1771792Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771792
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH3:18])[C:11]([CH3:17])=[C:12]([CH:16]=2)[C:13]([OH:15])=O)[CH:5]=[CH:6][CH:7]=1.C(Cl)(C(Cl)=O)=O.[NH2:25][C:26]1[C:27]([CH3:34])=[C:28]([OH:33])[CH:29]=[CH:30][C:31]=1[CH3:32].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C1COCC1.O.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH3:18])[C:11]([CH3:17])=[C:12]([CH:16]=2)[C:13]([NH:25][C:26]2[C:31]([CH3:32])=[CH:30][CH:29]=[C:28]([OH:33])[C:27]=2[CH3:34])=[O:15])[CH:5]=[CH:6][CH:7]=1

Komponenten

9

Edukt 4

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 141306083-Amino-2,4-dimethylphenolHCID 894435205-(3-Fluorophenyl)-2,3-dimethyl-benzoic acid

Produkt 1

HCID 894451745-(3-Fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)-2,3-dimethyl-benzamideAusbeute 51,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 5-(3-fluorophenyl)-2,3-dimethyl-benzoic acid (intermediate III(m)) (0.4 g, 1.6 mmol, 1.0 eq) in CH2Cl2 (15 mL) was added (COCl)2 (0.62 g, 4.9 mmol, 3.0 eq) and DMF (0.01 mL). The reaction mixture was stirred at room temperature for 1.5 h, then the solvent and excess reagent were removed under reduced pressure. The residue obtained was dissolved in THF (20 mL) and added dropwise to a mixture of 3-amino-2,4-dimethylphenol (intermediate X(c)) (260 mg, 1.9 mmol, 1.2 eq) and K2CO3 (0.9 g, 6.5 mmol, 4.0 eq) in THF (20 mL) at 0° C. The reaction mixture was stirred at room temperature for 1 h, then poured into water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether: EtOAc, 15:1 to 3:1) to give the title compound as a colorless oil (300 mg, 51%)

Aufarbeitung

  1. customthe solvent and excess reagent were removed under reduced pressure
  2. customThe residue obtained
  3. stirringThe reaction mixture was stirred at room temperature for 1 h
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography (petroleum ether: EtOAc, 15:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-0172cdfe520a4de6ae5e6723c56e7c59
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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