Methanesulfonic Acid → 2-(4-Nitrobenzyl)-5-propyl-1,3,4-oxadiazole

HRID 30641

반응식

HRID 30641 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][NH2:14])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:15](OC)(OC)(OC)[CH2:16][CH2:17][CH3:18].CS(O)(=O)=O.O1CCCC1>O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[O:12][C:15]([CH2:16][CH2:17][CH3:18])=[N:14][N:13]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 6395Methanesulfonic AcidHCID 8028TetrahydrofuranHCID 1235121,1,1-TrimethoxybutaneHCID 2873312-(4-Nitrophenyl)acetohydrazide

생성물 1

HCID 692088952-(4-Nitrobenzyl)-5-propyl-1,3,4-oxadiazole

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 2-(4-nitrophenyl)acetohydrazide (7.0 g), trimethyl orthobutyrate (16.01 g), methanesulfonic acid (0.69 g) and tetrahydrofuran (200 mL) was heated under reflux for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and 2-(4-nitrobenzyl)-5-propyl-1,3,4-oxadiazole was obtained as a colorless oil (7.73 g, yield 87%) from a fraction eluted with hexane-ethyl acetate (3:2-1:2, v/v).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d3f0feac829549ef83af5f08dda06d3d
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423159B2

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