Trifluoroacetic acid → HCID 23114766, compound

HRID 2080386Notes

Reaction equation

HRID 2080386 reaction equation
FC(F)(F)C(O)=O.C(OC(O[CH:16]([C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[F:31])[C:17]1[N:18]([CH3:23])[C:19]([Cl:22])=[CH:20][N:21]=1)=O)(C)(C)C.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([SH:39])=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([S:39][CH:16]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])[C:17]2[N:18]([CH3:23])[C:19]([Cl:22])=[CH:20][N:21]=2)=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 23114840HCID 23114840, compound

Product 1

HCID 23114766HCID 23114766, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Trifluoroacetic acid (10 ml) was added to the 2-[(t-butoxycarbonyloxy)-(2,5-difluorophenyl)methyl]-1-methyl-5-chloro-1H-imidazole (404 mg, 1.13 mmol) obtained in Referential Example 14. The resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. Dioxane was added to the residue, followed by further concentration under reduced pressure. The residue was dissolved in thionyl chloride (2.0 ml) and to the resulting solution was added a drop of dimethylformamide. The mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated under reduced pressure. Dioxane was added to the residue, followed by further concentration under reduced pressure. The residue was dissolved in dimethylformamide (5.0 ml). To the resulting solution were added 4-chlorobenzenethiol (244 mg, 1.69 mmol) and potassium carbonate (936 mg, 6.78 mmol). The resulting mixture was stirred at 50° C. for 2 hours. The reaction mixture was allowed to stand until it became room temperature. Ethyl ether (60 ml) was added. The resulting mixture was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1 to 5:1) to give the title compound (195 mg, 89%) as a colorless oil.

Workup

  1. customobtained in Referential Example 14
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionDioxane was added to the residue
  4. concentrationfollowed by further concentration under reduced pressure
  5. dissolutionThe residue was dissolved in thionyl chloride (2.0 ml) and to the resulting solution
  6. additionwas added a drop of dimethylformamide
  7. stirringThe mixture was stirred at room temperature for 17 hours
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. additionDioxane was added to the residue
  10. concentrationfollowed by further concentration under reduced pressure
  11. dissolutionThe residue was dissolved in dimethylformamide (5.0 ml)
  12. stirringThe resulting mixture was stirred at 50° C. for 2 hours
  13. custombecame room temperature
  14. washThe resulting mixture was washed with water and brine
  15. dry with materialdried over anhydrous magnesium sulfate
  16. concentrationconcentrated under reduced pressure
  17. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1 to 5:1)

Sources & evidence

ORD record
ord-2a413c823d6d42ec984ed47da2cb0ddc
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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