HCID 11544308, compound → HCID 11515065, compound

HRID 2056617Notes

Reaction equation

HRID 2056617 reaction equation
[N+]([O-])([O-])=[O:2].[NH4+].[Ce].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=1[C:15]1[S:16][C:17]2[C:18](=[C:20](N)[C:21]([O:26][CH3:27])=[CH:22][C:23]=2[O:24]C)[N:19]=1>O.C(OCC)(=O)C>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=1[C:15]1[S:16][C:17]2[C:23](=[O:24])[CH:22]=[C:21]([O:26][CH3:27])[C:20](=[O:2])[C:18]=2[N:19]=1

Participants

5

Reactant 2

HCID 11544308HCID 11544308, compoundHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 11515065HCID 11515065, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.22 g of cerium ammonium nitrate (2.23 mmol, 2.1 equivalents) in 8 ml of water is added to 343 mg (1.06 mmol) of 2-(2,6-difluorophenyl)-5,7-dimethoxy-1,3-benzothiazol-4-amine in solution in 25 ml of ethyl acetate. The reaction mixture is maintained under vigorous stirring at ambient temperature for 1 hour 30 minutes then the organic phase is separated and washed with 3 times 20 ml of water, then dried over magnesium sulphate, filtered and the solvent is evaporated off under reduced pressure. The residue is purified by chromatography on a silica column (eluent: ethyl acetate/heptane: 3/7) and 280 mg (yield=86%) of 2-(2,6-difluorophenyl)-5-methoxy-1,3-benzothiazole-4,7-dione is obtained in the form of yellow powder.

Workup

  1. temperatureThe reaction mixture is maintained
  2. customthe organic phase is separated
  3. washwashed with 3 times 20 ml of water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent is evaporated off under reduced pressure
  7. customThe residue is purified by chromatography on a silica column (eluent: ethyl acetate/heptane: 3/7)

Sources & evidence

ORD record
ord-4693c7d8f8f1487ba1a17d0347356c1a
Source dataset
uspto-grants-2008_02
Patent number
US07335674B2

Reaction notes

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