N-bromobutanimide → 3-[3-[3-(Bromomethyl)-2-thienyl]-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

HRID 48968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 48968
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[C:11]2[CH:12]=[C:13]([N:16]3[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]([CH3:27])[C:17]3=[O:28])[CH:14]=[CH:15][C:10]=2[S:9][N:8]=1.[Br:29]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:29][CH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[C:11]2[CH:12]=[C:13]([N:16]3[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]([CH3:27])[C:17]3=[O:28])[CH:14]=[CH:15][C:10]=2[S:9][N:8]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 206341763-[3-[3-(Methyl)-2-thienyl]-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

Produkt 1

HCID 206342133-[3-[3-(Bromomethyl)-2-thienyl]-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracilAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a mixture of 3-[3-[3-(methyl)-2-thienyl]-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil(0.420 g, 0.993 mmol) and carbon tetrachloride is added N-bromosuccinimide (0.200 g, 1.12 mmol) and benzoyl peroxide (10.0 mg). The resultant mixture is stirred overnight at reflux, cooled and filtered. The filtrate is concentrated in vacuo and the residue partitioned between water and methylene chloride. The organic layer is washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel with methylene chloride-diethyl ether to afford a pale yellow oil, which is crystallized in diethyl ether to afford the title compound as a cream-colored solid (0.340 g, 68.1%, mp 169° C.(dec)) which is identified by NMR spectral analysis.

Aufarbeitung

  1. temperatureat reflux
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue partitioned between water and methylene chloride
  6. washThe organic layer is washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue is chromatographed on silica gel with methylene chloride-diethyl ether
  10. customto afford a pale yellow oil, which
  11. customis crystallized in diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-b9e0cdb8cde043c4858f325736af3083
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706663B2

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