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

HRID 452680ノート

反応式

HRID 452680 の反応式
[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

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 697163-(Trifluoromethyl)benzyl chlorideHCID 178527938HCID 178527938、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6503a605ccbf430aa7b8c91a4b893aeb
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

反応ノート

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