Acetic Acid → 3-[3-(6-Methoxy-3,4-xylyl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

HRID 277356

Reaktionsgleichung

Reaktionsgleichung von HRID 277356
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([C:10]3[C:15]([O:16][CH3:17])=[CH:14][C:13]([CH3:18])=[C:12]([CH3:19])[CH:11]=3)[C:6]=2[CH:20]=1.CN(C)[C:23]1[O:24][C:25](=[O:33])[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=1.C(O)(=O)C.O>C(Cl)Cl.C(OCC)C>[CH3:17][O:16][C:15]1[C:10]([C:7]2[C:6]3[CH:20]=[C:2]([N:1]4[C:25](=[O:33])[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[NH:28][C:23]4=[O:24])[CH:3]=[CH:4][C:5]=3[S:9][N:8]=2)=[CH:11][C:12]([CH3:19])=[C:13]([CH3:18])[CH:14]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 183145035-Amino-3-(6-methoxy-3,4-xylyl)-1,2-benzisothiazole

Produkt 1

HCID 154776123-[3-(6-Methoxy-3,4-xylyl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedioneAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 5-amino-3-(6-methoxy-3,4-xylyl)-1,2-benzisothiazole (8.53 g, 30.0 mmol), 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (6.87 g, 33.0 mmol) and acetic acid is refluxed for 2 hours, cooled, and poured into water. The resultant aqueous mixture is filtered to obtain a solid. A solution of the solid in methylene chloride is washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an oil. Column chromatography of the oil using silica gel and a 5% diethyl ether in methylene chloride solution gives the title product as a yellow foam (8.37 g, 62.0%) which is identified by NMR spectral analyses.

Aufarbeitung

  1. temperatureis refluxed for 2 hours
  2. temperaturecooled
  3. filtrationThe resultant aqueous mixture is filtered
  4. customto obtain a solid
  5. washA solution of the solid in methylene chloride is washed sequentially with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain an oil

Quellen und Nachweise

ORD-Eintrag
ord-ffb87ddadc4547c0ae76559fff954cf8
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355796B1

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