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

HRID 277397

Reaction equation

HRID 277397 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(cyclohexanecarbonitrile) (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, 100%) 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-894b156accfa418d876b9b1b05179d1c
Source dataset
uspto-grants-2002_03
Patent number
US06355796B1

Linked notes

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