Potassium Iodide → 3-({[1,5-bis(4-methoxyphenyl)-1H-1,2,4-triazol-3-yl]oxy}methyl)-1,2,4-oxadiazole

HRID 584751노트

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HRID 584751 반응식
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[N:20][C:19]([OH:30])=[N:18]2)=[CH:13][CH:12]=1.Cl[CH2:32][C:33]1[N:37]=[CH:36][O:35][N:34]=1>CN(C)C=O.O.C(OCC)(=O)C>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([N:17]2[C:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[N:20][C:19]([O:30][CH2:32][C:33]3[N:37]=[CH:36][O:35][N:34]=3)=[N:18]2)=[CH:15][CH:16]=1

참가 물질

8

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27357653-(Chloromethyl)-1,2,4-oxadiazoleHCID 1784890151,5-bis(4-methoxyphenyl)-1H-1,2,4-triazol-3-ol

생성물 1

HCID 101997023-({[1,5-bis(4-methoxyphenyl)-1H-1,2,4-triazol-3-yl]oxy}methyl)-1,2,4-oxadiazole수율 43.1%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

Potassium carbonate (279 mg, 2.02 mmol) and potassium iodide (335 mg, 2.02 mmol) was added to a solution of 1,5-bis(4-methoxyphenyl)-1H-1,2,4-triazol-3-ol (200 mg, 0.673 mmol) in dimethylformamide (2 mL). After 5 minutes stirring, 3-(chloromethyl)-1,2,4-oxadiazole (239 mg, 2.02 mmol) was added to the mixture and the mixture was heated at 100° C. for 1 hour. After cooling, ethyl acetate and water were poured into the mixture. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by preparative-TLC (toluene-ethyl acetate 4:1). The desired product was triturated with isopropylether, isolated by filtration, and dried in vacuo to give 3-({[1,5-bis(4-methoxyphenyl)-1H-1,2,4-triazol-3-yl]oxy}methyl)-1,2,4-oxadiazole (110 mg, 43.1% yield).

후처리

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by preparative-TLC (toluene-ethyl acetate 4:1)
  7. customThe desired product was triturated with isopropylether
  8. customisolated by filtration
  9. customdried in vacuo

출처 및 근거

ORD 기록
ord-77166dba83994b04bb0ba0b4e45509c1
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06927230B2

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