Hydrochloric Acid → HCID 18314487, Verbindung

HRID 369587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 369587
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]=2[CH:18]=1.CN(C)[C:21]1[O:22][C:23](=[O:31])[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[N:26]=1.[C:33](=O)([O-])[O-].[K+].[K+].IC.Cl>C(O)(=O)C.CN(C)C=O.C(Cl)Cl.C(OCC)(=O)C>[CH3:33][N:26]1[C:25]([C:27]([F:30])([F:29])[F:28])=[CH:24][C:23](=[O:31])[N:1]([C:2]2[CH:3]=[CH:4][C:5]3[S:9][N:8]=[C:7]([C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]=3[CH:18]=2)[C:21]1=[O:22]

Komponenten

10

Edukt 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 18314476HCID 18314476, Verbindung

Produkt 1

HCID 18314487HCID 18314487, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of ethyl 5-amino-α,α-dimethyl-1,2-benzisothiazole-3-acetate (0.546 g, 2.06 mmol) and 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (0.430 g, 2.06 mmol) in acetic acid is refluxed for 4.5 hours, concentrated in vacuo, and diluted with saturated sodium hydrogen carbonate solution. The resultant aqueous mixture is extracted with methylene chloride. The combined organic extracts are washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a brown foam. A solution of the foam in N,N-dimethylformamide is treated with potassium carbonate (0.312 g, 2.25 mmol), stirred for one hour, treated with iodomethane (0.420 mL, 6.70 mmol), stirred overnight at room temperature, and poured into an ice-water mixture containing 20 mL of concentrated hydrochloric acid. The resultant aqueous mixture is extracted with methylene chloride. The combined organic extracts are washed sequentially with 10% hydrochloric acid, water, saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a brown oil. Column chromatography of the oil using silica gel and a 33% ethyl acetate in methylene chloride solution affords a pink foam which is recrystallized from ethanol to give the title product as pink crystals, mp 164-167° C.

Aufarbeitung

  1. temperatureis refluxed for 4.5 hours
  2. concentrationconcentrated in vacuo
  3. additiondiluted with saturated sodium hydrogen carbonate solution
  4. extractionThe resultant aqueous mixture is extracted with methylene chloride
  5. washThe combined organic extracts are washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a brown foam
  9. stirringstirred overnight at room temperature
  10. extractionThe resultant aqueous mixture is extracted with methylene chloride
  11. washThe combined organic extracts are washed sequentially with 10% hydrochloric acid, water, saturated sodium hydrogen carbonate solution and water
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated in vacuo
  14. customto obtain a brown oil
  15. customis recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-78a646ff97634720b51a331b066b78eb
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140270

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