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

HRID 452681

反応式

HRID 452681 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-01ba171fa41440188f5ac899891d28f9
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

関連ノート

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