Ethyl chloroformate → 5-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one

HRID 30647

반응식

HRID 30647 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](Cl)(=O)[O:16]CC.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C[Si](C)(C)O[Si](C)(C)C>O.ClC1C=CC=CC=1Cl.CN(C)C(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[O:12][C:15](=[O:16])[NH:14][N:13]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

참가 물질

8

반응물 4

HCID 10928Ethyl chloroformateHCID 14812Phosphorus oxide (P4O10)HCID 24764HexamethyldisiloxaneHCID 2873312-(4-Nitrophenyl)acetohydrazide

생성물 1

HCID 218227135-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one수율 51.2%

시약·촉매·용매 3

HCID 962Water용매2회HCID 72391,2-Dichlorobenzene용매HCID 31374Dimethylacetamide용매

실험 절차

A mixture of 2-(4-nitrophenyl)acetohydrazide (0.50 g), ethyl chlorocarbonate (0.34 g) and N,N-dimethylacetamide (10 mL) was stirred at room temperature for 1 hr. Water was added to 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 to give colorless crystals. A mixture of the obtained crystals, diphosphorus pentaoxide (1.50 g), hexamethyldisiloxane (2.96 g) and 1,2-dichlorobenzene (10 mL) was stirred at 160° C. for 2 hrs. Water was added to 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 to give 5-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one as pale-yellow crystals (0.29 g, yield 50%). Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 170-171° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give colorless crystals
  6. stirringwas stirred at 160° C. for 2 hrs
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-eaed8ae426304e12b0a1ad020e1f21cf
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423159B2

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