Dimethylacetamide → HCID 58780781、化合物

HRID 30666

反応式

HRID 30666 の反応式
[OH:1][N:2]=[C:3]([NH2:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.CN(C)C(=O)C.[C:21](Cl)(=O)[CH2:22][CH3:23]>O>[CH2:22]([C:23]1[O:1][N:2]=[C:3]([CH2:4][C:5]2[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=2)[N:14]=1)[CH3:21]

参加物

5

反応物 3

HCID 31374DimethylacetamideHCID 62324Propionyl chlorideHCID 308292N-hydroxy-2-(4-nitrophenyl)acetamidine

生成物 1

HCID 58780781HCID 58780781、化合物収率 60%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of N′-hydroxy-2-(4-nitrophenyl)ethanimidamide (6.17 g) and N,N-dimethylacetamide (50 mL) was added propionyl chloride (3.22 g) at room temperature. The reaction mixture was stirred at room temperature for 2 hrs. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. A mixture of the obtained residue and xylene (200 mL) was heated under reflux for 15 hrs. with azeotropic dehydration. The reaction mixture was concentrated and the obtained residue was subjected to silica gel column chromatography to give 5-ethyl-3-(4-nitrobenzyl)-1,2,4-oxadiazole as brown crystals (4.40 g, yield 60%) from a fraction eluted with hexane-ethyl acetate (3:1-2:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 69-70° C.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. additionA mixture of the obtained residue and xylene (200 mL)
  6. temperaturewas heated
  7. temperatureunder reflux for 15 hrs
  8. concentrationThe reaction mixture was concentrated

出典と根拠

ORDレコード
ord-27532675ebc04c29835801ea175e9cac
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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