Potassium Carbonate → 6-[5-[[3-(Trifluoromethyl)benzyl]thio]-1,3,4-oxadiazol-2-yl]benzothiazole

HRID 452680Notes

Reaction equation

HRID 452680 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([C:10]3[O:14][C:13]([SH:15])=[N:12][N:11]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[F:16][C:17]([F:27])([F:26])[C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[F:16][C:17]([F:26])([F:27])[C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21][S:15][C:13]1[O:14][C:10]([C:7]2[CH:8]=[CH:9][C:4]3[N:3]=[CH:2][S:1][C:5]=3[CH:6]=2)=[N:11][N:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 697163-(Trifluoromethyl)benzyl chlorideHCID 178527938HCID 178527938, compound

Product 1

HCID 686640606-[5-[[3-(Trifluoromethyl)benzyl]thio]-1,3,4-oxadiazol-2-yl]benzothiazoleYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5-(benzothiazol-6-yl)-1,3,4-oxadiazole-2-thiol (235 mg, 1.00 mmol), 3-(trifluoromethyl)benzyl chloride (0.186 mL, 1.20 mmol), and potassium carbonate (207 mg, 1.50 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 5 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (tetrahydrofuran) and recrystallized from hexane/tetrahydrofuran to give the title compound (321 mg, yield 82%) as colorless crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (tetrahydrofuran)
  5. customrecrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-6503a605ccbf430aa7b8c91a4b893aeb
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

Loading…