N-bromobutanimide → 5-Amino-4-bromo-6-fluoro-3-methyl-1,2-benzisothiazole

HRID 636059

Reaktionsgleichung

Reaktionsgleichung von HRID 636059
[NH2:1][C:2]1[C:3]([F:12])=[CH:4][C:5]2[S:9][N:8]=[C:7]([CH3:10])[C:6]=2[CH:11]=1.[Br:13]N1C(=O)CCC1=O>ClCCCl.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>[NH2:1][C:2]1[C:3]([F:12])=[CH:4][C:5]2[S:9][N:8]=[C:7]([CH3:10])[C:6]=2[C:11]=1[Br:13]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimide2×HCID 120568325-Amino-6-fluoro-3-methyl-1,2-benzisothiazole

Produkt 1

HCID 183144995-Amino-4-bromo-6-fluoro-3-methyl-1,2-benzisothiazoleAusbeute 101,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 749781,1'-Azobis(cyclohexanecarbonitrile)KatalysatorHCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 5-amino-6-fluoro-3-methyl-1,2-benzisothiazole (0.600 g, 0.00329 mol) in 1,2-dichloroethane is added N-bromosuccinimide (0.586 g, 0.00329 mol) followed by 1,1′-azobis(cyclohexanecarbo-nitrile) (0.0200 g). The mixture is stirred two hours at 70° C., additional N-bromosuccinimide (0.240 g, 0.00135 mol) is added, and the mixture is stirred 40 minutes at 70° C. The mixture is then cooled to room temperature, filtered and concentrated in vacuo to obtain a residue. The residue is chromatographed on silica gel to give the title compound (0.870 g, 100w) which is identified by NMR spectral analysis.

Aufarbeitung

  1. stirringthe mixture is stirred 40 minutes at 70° C
  2. temperatureThe mixture is then cooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue
  6. customThe residue is chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-efff88441c2240e6ace91946073b19d2
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06191275B1

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