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

HRID 636059

Reaction equation

HRID 636059 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 183144995-Amino-4-bromo-6-fluoro-3-methyl-1,2-benzisothiazoleYield 101.3%

Reagents, catalysts & solvents 2

HCID 749781,1'-Azobis(cyclohexanecarbonitrile)CatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-efff88441c2240e6ace91946073b19d2
Source dataset
uspto-grants-2001_02
Patent number
US06191275B1

Linked notes

Loading…