1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-[3-(6-Methoxy-m-tolyl)-1,2-benzisothiazol-5-yl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

HRID 428384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 428384
C(O[C:4]([NH:6]/[C:7](/[C:14]([F:17])([F:16])[F:15])=[CH:8]\[C:9]([O:11]CC)=O)=[O:5])C.[NH2:18][C:19]1[CH:20]=[CH:21][C:22]2[S:26][N:25]=[C:24]([C:27]3[CH:28]=[C:29]([CH3:35])[C:30]([O:33][CH3:34])=[CH:31][CH:32]=3)[C:23]=2[CH:36]=1.N12CCCN=C1CCCCC2>C1(C)C(C)=CC=CC=1>[CH3:34][O:33][C:30]1[C:29]([CH3:35])=[CH:28][C:27]([C:24]2[C:23]3[CH:36]=[C:19]([N:18]4[C:9](=[O:11])[CH:8]=[C:7]([C:14]([F:15])([F:16])[F:17])[NH:6][C:4]4=[O:5])[CH:20]=[CH:21][C:22]=3[S:26][N:25]=2)=[CH:32][CH:31]=1

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11288292Ethyl 3-[(ethoxycarbonyl)amino]-4,4,4-trifluorocrotonateHCID 698320455-Amino-3-(6-methoxy-m-tolyl)-1,2-benzisothiazole

Produkt 1

HCID 701000153-[3-(6-Methoxy-m-tolyl)-1,2-benzisothiazol-5-yl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedioneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of ethyl 3-[(ethoxycarbonyl)amino]-4,4,4-trifluorocrotonate, (Z)-(2.04 g, 8 mmol), 5-amino-3-(6-methoxy-m-tolyl)-1,2-benzisothiazole (2.59 g, 9.6 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU, 1.46 g, 9.6 mmol) in xylene (15 mL) is heated at 110° C. for 6 hours, cooled, and quenched with ethyl acetate and water. The resultant mixture is extracted with ethyl acetate. The organic extracts are combined, washed with aqueous 2 N hydrochloric acid, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to obtain a foam. Flash chromatography of the foam using silica gel and a 3:7 ethyl acetate/hexanes solution gives the title product as a solid (2.5 g, 72% yield) which is identified by 1H and 19F NMR spectral analyses.

Aufarbeitung

  1. temperaturecooled
  2. customquenched with ethyl acetate and water
  3. extractionThe resultant mixture is extracted with ethyl acetate
  4. washwashed with aqueous 2 N hydrochloric acid
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto obtain a foam

Quellen und Nachweise

ORD-Eintrag
ord-feda41e2792f4755afcd05c724495655
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313295B1

Notizen zur Reaktion

Wird geladen…