HCID 11500537, compound → HCID 11716488, compound

HRID 2056616Notes

Reaction equation

HRID 2056616 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[S:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1>[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[F:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([F:20])[C:14]=1[C:12]1[S:13][C:4]2[C:3]([O:2][CH3:1])=[CH:8][C:7]([O:9][CH3:10])=[CH:6][C:5]=2[N:11]=1

Participants

3

Reactant 1

HCID 11500537HCID 11500537, compound

Product 1

HCID 11716488HCID 11716488, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 178511488HCID 178511488, compoundCatalyst

Procedure

170 ml (103 mmol; 3 equivalents) of a freshly prepared 20% aqueous solution of potassium ferricyanide is added to 10.3 g (33.3 mmol) of N-(3,5-dimethoxyphenyl)-2,6-difluorobenzenecarbothioamide dissolved in 150 ml of a 1.5M soda solution. The reaction medium is maintained under stirring at ambient temperature for 24 hours, then the beige precipitate formed is filtered, washed with water and dried (6.8 g; yield=66%). The mother liquors can be extracted by 3 times 75 ml of dichloromethane, then the organic phases are washed with a saturated solution of sodium chloride. After concentration under reduced pressure, the residue obtained can be purified on a silica column (eluent: ethyl acetate/heptane: 1/3) in order to provide another 2 g of expected product (overall yield=86%). Melting point: 136-138° C.

Workup

  1. dissolutiondissolved in 150 ml of a 1.5M soda solution
  2. temperatureThe reaction medium is maintained
  3. customthe beige precipitate formed
  4. filtrationis filtered
  5. washwashed with water
  6. customdried (6.8 g; yield=66%)
  7. extractionThe mother liquors can be extracted by 3 times 75 ml of dichloromethane
  8. washthe organic phases are washed with a saturated solution of sodium chloride
  9. concentrationAfter concentration under reduced pressure
  10. customthe residue obtained can
  11. custombe purified on a silica column (eluent: ethyl acetate/heptane: 1/3) in order

Sources & evidence

ORD record
ord-fa195bf1513542a2b799c5f92dc034bf
Source dataset
uspto-grants-2008_02
Patent number
US07335674B2

Reaction notes

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