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Pivaloyl chloride → 5-(t-Butyl)-3-(5,6-dichloro-3-pyridinyl)-1,2,4-oxadiazole

HRID 368281
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HRID 368281 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[NH:12])[NH:10][OH:11])[CH:5]=[N:6][C:7]=1[Cl:8].[CH3:13][C:14]([CH3:19])([CH3:18])[C:15](Cl)=O>C1(C)C=CC=CC=1>[C:14]([C:19]1[O:11][N:10]=[C:9]([C:4]2[CH:5]=[N:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[N:12]=1)([CH3:18])([CH3:15])[CH3:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 62493Pivaloyl chlorideHCID 178513387HCID 178513387, 화합물

생성물 1

HCID 232882825-(t-Butyl)-3-(5,6-dichloro-3-pyridinyl)-1,2,4-oxadiazole수율 68%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

5,6-Dichloro-N-hydroxy-3-pyridinecarboximidamide (3.0 g, 0.015 mol) was slurried in toluene (30 mL) and trimethylacetyl chloride (1.93 g, 0.016 mol) added. The mixture was stirred at room temperature for one hour and then heated under reflux conditions for four hours. This was then cooled and filtered through Celite, washing with additional toluene (20 mL). Evaporation of the solvent under reduced pressure and purification of the residue by chromatography over silica (0-10% ethyl acetate:hexane) gave the desired product as a white solid (2.77 g, 68%).

후처리

  1. temperatureheated under reflux conditions for four hours
  2. temperatureThis was then cooled
  3. filtrationfiltered through Celite
  4. washwashing with additional toluene (20 mL)
  5. customEvaporation of the solvent
  6. customunder reduced pressure and purification of the residue by chromatography over silica (0-10% ethyl acetate:hexane)

출처 및 근거

ORD 기록
ord-c0773ffbf30d4005851044f0297e85dc
출처 데이터셋
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06133294

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