Oxalyl chloride → 5-(3-Fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)-2-methoxy-3-methyl-benzamide

HRID 1771796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771796
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH3:19])[C:11]([O:17][CH3:18])=[C:12]([CH:16]=2)[C:13]([OH:15])=O)[CH:5]=[CH:6][CH:7]=1.C(Cl)(C(Cl)=O)=O.[NH2:26][C:27]1[C:28]([CH3:35])=[C:29]([OH:34])[CH:30]=[CH:31][C:32]=1[CH3:33].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C.C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH3:19])[C:11]([O:17][CH3:18])=[C:12]([CH:16]=2)[C:13]([NH:26][C:27]2[C:32]([CH3:33])=[CH:31][CH:30]=[C:29]([OH:34])[C:28]=2[CH3:35])=[O:15])[CH:5]=[CH:6][CH:7]=1

Komponenten

9

Edukt 4

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 141306083-Amino-2,4-dimethylphenolHCID 894437175-(3-Fluorophenyl)-2-methoxy-3-methyl-benzoic acid

Produkt 1

HCID 894435135-(3-Fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)-2-methoxy-3-methyl-benzamideAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 5-(3-fluorophenyl)-2-methoxy-3-methyl-benzoic acid (intermediate III(k)) (400 mg, 1.5 mmol, 1.1 eq) in CH2Cl2 (8 mL) was added (COCl)2 (585 mg, 4.6 mmol, 3.3 eq) and DMF (3 drops). The reaction mixture was stirred at room temperature for 1 h. The resulting mixture was concentrated under reduced pressure to remove the solvent and excess reagent and the residue obtained was dissolved in THF (8 mL) and added dropwise to a solution of 3-amino-2,4-dimethylphenol (intermediate X(c)) (192 mg, 1.4 mmol, 1.0 eq) and NaHCO3 (587 mg, 7.0 mmol, 5.0 eq) in THF (6 mL) at 0° C. After the addition was complete the reaction mixture was allowed to warm to room temperature and was stirred for 2 h. The resulting mixture was 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 obtained was purified by column chromatography (petroleum ether: EtOAc, 10:1 to 5:1, then DCM: MeOH, 20:1) to give the title compound as a yellow solid (436 mg 82%).

Aufarbeitung

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. customto remove the solvent and excess reagent
  3. customthe residue obtained
  4. additionAfter the addition
  5. temperatureto warm to room temperature
  6. stirringwas stirred for 2 h
  7. extractionextracted with EtOAc
  8. washThe combined organic extracts were washed with water and brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. customThe residue obtained
  13. customwas purified by column chromatography (petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-f060430cd1f54f93b973b7adb0f98274
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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