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

HRID 30647

反応式

HRID 30647 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 72391,2-Dichlorobenzene溶媒HCID 31374Dimethylacetamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eaed8ae426304e12b0a1ad020e1f21cf
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

関連ノート

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