HCID 16734358, compound → HCID 69220416, compound

HRID 2056621Notes

Reaction equation

HRID 2056621 reaction equation
[N+]([O-])([O-])=[O:2].[NH4+].[Ce].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25]C)[C:17]=3[N:18]=2)=[CH:10][CH:9]=1>C(OCC)(=O)C>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]3[C:22](=[O:2])[C:21]([O:23][CH3:24])=[CH:20][C:19](=[O:25])[C:17]=3[N:18]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 16734358HCID 16734358, compoundHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 69220416HCID 69220416, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

63 ml of a freshly prepared 0.65 M cerium ammonium nitrate solution is added, dropwise, to 3.8 g (13.1 mmol) of 2-(4-fluorophenyl)-4,6-dimethoxy-1,3-benzothiazole in solution in 100 ml of ethyl acetate. The reaction mixture is maintained under stirring at ambient temperature for 3 hours then the aqueous phase is separated and washed with 3 times 75 ml of ethyl acetate. The organic phases are combined, dried over sodium sulphate and the solvents are evaporated off under reduced pressure. The residue is purified by chromatography on a silica column (eluent: ethyl acetate/heptane mixture 1:3) in order to provide 0.6 g (16% yield) of expected product.

Workup

  1. temperatureThe reaction mixture is maintained
  2. customthe aqueous phase is separated
  3. washwashed with 3 times 75 ml of ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. customthe solvents are evaporated off under reduced pressure
  6. customThe residue is purified by chromatography on a silica column (eluent: ethyl acetate/heptane mixture 1:3) in order

Sources & evidence

ORD record
ord-9d760c1892744ce6a55fd99a27095ad1
Source dataset
uspto-grants-2008_02
Patent number
US07335674B2

Reaction notes

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