2,6-Dichloro-isonicotinoyl chloride → 6-(2,6-dichloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

HRID 469317

Reaktionsgleichung

Reaktionsgleichung von HRID 469317
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](Cl)=[O:9])[CH:5]=[C:4]([Cl:11])[N:3]=1.[CH3:12][C:13]1[C:18]2[NH:19][C:20](=[O:22])[O:21][C:17]=2[CH:16]=[CH:15][CH:14]=1.[Cl-].[Cl-].[Cl-].[Al+3]>CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:15]2[CH:14]=[C:13]([CH3:12])[C:18]3[NH:19][C:20](=[O:22])[O:21][C:17]=3[CH:16]=2)=[O:9])[CH:5]=[C:4]([Cl:11])[N:3]=1

Komponenten

5

Edukt 3

HCID 27816432,6-Dichloro-isonicotinoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 127093364-Methyl-3H-benzooxazol-2-one

Produkt 1

HCID 581812126-(2,6-dichloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3.00 g (14.3 mmol) 2,6-dichloropyridine-4-carboxylic acid chloride, 1.80 g (11.0 mmol) 4-methyl-3H-benzoxazol-2-one and 9.47 g (71.0 mmol) aluminium trichloride were combined and heated for 2 h to 125° C. with stirring. Then the mixture was decomposed with ice water and EtOAc and the phases were separated. The aqueous phase was extracted several times with EtOAc. The organic phases were combined, dried on sodium sulphate, filtered and the filtrate was evaporated down i. vac. The residue was triturated with diethyl ether, the precipitate was suction filtered and dried i. vac.

Aufarbeitung

  1. temperatureheated for 2 h to 125° C.
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted several times with EtOAc
  4. customdried on sodium sulphate
  5. filtrationfiltered
  6. customthe filtrate was evaporated down i
  7. customThe residue was triturated with diethyl ether
  8. filtrationfiltered
  9. customdried i

Quellen und Nachweise

ORD-Eintrag
ord-d8a2718c0911453f9d47a4de7cf71a7f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629137B2

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