4-Toluenesulfonyl chloride → 6-[5-[2-[3-(Trifluoromethyl)phenyl]ethyl]-1,3,4-oxadiazol-2-yl]benzothiazole

HRID 452681Notes

Reaction equation

HRID 452681 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([NH:13][NH:14][C:15]([C:17]2[CH:25]=[CH:24][C:20]3[N:21]=[CH:22][S:23][C:19]=3[CH:18]=2)=O)=[O:12])[CH:6]=[CH:7][CH:8]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1.C(OCC)(=O)C>[F:27][C:2]([F:1])([F:26])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[O:12][C:15]([C:17]3[CH:25]=[CH:24][C:20]4[N:21]=[CH:22][S:23][C:19]=4[CH:18]=3)=[N:14][N:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68664426N'-[3-[3-(trifluoromethyl)phenyl]propionyl]benzothiazole-6-carbohydrazide

Product 1

HCID 686631086-[5-[2-[3-(Trifluoromethyl)phenyl]ethyl]-1,3,4-oxadiazol-2-yl]benzothiazoleYield 75%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N′-[3-[3-(trifluoromethyl)phenyl]propionyl]benzothiazole-6-carbohydrazide (433 mg, 1.10 mmol) and p-toluenesulfonyl chloride (419 mg, 2.20 mmol) in pyridine (5 mL) was stirred under an argon atmosphere at 80° C. for 16 hr. After cooling, the reaction mixture was diluted with ethyl acetate, washed with 0.1M hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/1) and recrystallized from hexane/ethyl acetate to give the title compound (308 mg, yield 75%) as colorless crystals.

Workup

  1. temperatureAfter cooling
  2. washwashed with 0.1M hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/1)
  6. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-01ba171fa41440188f5ac899891d28f9
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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