Tetrahydrofuran → N-{[2,3-dichloro-4-cyano-5-(3,4-dichlorophenyl)pyrrol-1-yl]methyl}acetamide

HRID 654132

反応式

HRID 654132 の反応式
[Cl:1][C:2]1[C:3]([C:16]#[N:17])=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[NH:5][C:6]=1[Cl:7].O1CCCC1.[H-].[Na+].C(O)(=O)C.O[CH2:30][NH:31][C:32](=[O:34])[CH3:33]>O.C(Cl)Cl.C(OCC)(=O)C.C(Cl)Cl>[Cl:7][C:6]1[N:5]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)=[C:3]([C:16]#[N:17])[C:2]=1[Cl:1]

参加物

8

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 24758Sodium hydrideHCID 1835554,5-dichloro-2-(3,4-dichlorophenyl)-1H-pyrrole-3-carbonitrileHCID 86745977N-(hydroxymethyl)acetamide acetate

生成物 1

HCID 19888638N-{[2,3-dichloro-4-cyano-5-(3,4-dichlorophenyl)pyrrol-1-yl]methyl}acetamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

A slurry of 4,5-dichloro-2-(3,4-dichlorophenyl)pyrrole-3-carbonitrile (15.3 g, 0.05 mol) and tetrahydrofuran (80 mL) is cooled to 10° C. and treated portionwise over 20 minutes with sodium hydride (2.2 g, 60% in oil, 0.055 mol). After stirring for 15 minutes this solution is added dropwise to a 50° C. solution of N-(hydroxymethyl)acetamide acetate (ester) (9.18 g, 0.07 mol) and tetrahydrofuran (20 mL). The reaction mixture is refluxed for two hours, cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic extract is washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a solid. Flash chromatography of the solid on silica gel packed in methylene chloride using ethyl acetate/methylene chloride solutions as eluents gives a solid. Recrystallization of the solid from ethyl acetate gives the title product as off white crystals (5.35 g, mp 162°-162.5° C.) which is identified by IR and NMR spectral analyses.

後処理

  1. temperatureThe reaction mixture is refluxed for two hours
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washis washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a solid
  8. customgives a solid
  9. customRecrystallization of the solid from ethyl acetate

出典と根拠

ORDレコード
ord-634bb40dd24547a7b237b95582161f04
出典データセット
uspto-grants-1992_07
特許番号
US05130328

関連ノート

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