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

HRID 452681

반응식

HRID 452681 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-01ba171fa41440188f5ac899891d28f9
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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