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

HRID 452680노트

반응식

HRID 452680 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6503a605ccbf430aa7b8c91a4b893aeb
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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