Pyrrole → (2-Chloro-3-nitrophenyl)-1H-pyrrol-1-ylmethanone

HRID 895158ノート

反応式

HRID 895158 の反応式
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[NH:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1)=[O:6]

参加物

8

反応物 4

HCID 8027PyrroleHCID 8471TriethylamineHCID 198702-Chloro-3-nitrobenzoic acidHCID 24386Thionyl Chloride

生成物 1

HCID 22385748(2-Chloro-3-nitrophenyl)-1H-pyrrol-1-ylmethanone収率 97%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-Chloro-3-nitrobenzoic acid (2 g, 10.0 mmol) and thionyl chloride (30 ml) were mixed at room temperature, and 4-dimethylaminopyridine (122 mg, 1.00 mmol) was added. The reaction mixture was refluxed for 12 hours and then concentrated to give a crude acid chloride. The acid chloride mentioned above was added to a solution of pyrrole (3.5 ml, 50.0 mmol) and triethylamine (7.0 ml, 50.0 mmol) in methylene chloride (80 ml) at room temperature. The reaction mixture was stirred at the same temperature for 6 hours and diluted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, filtered, and concentrated to give a crude compound. The crude compound was purified by silica gel column chromatography (hexane:ethyl acetate, 1:0-7:3) to give the title compound (2.43 g) as a yellow oil.

後処理

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. concentrationconcentrated
  3. customto give a crude acid chloride
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude compound
  9. customThe crude compound was purified by silica gel column chromatography (hexane:ethyl acetate, 1:0-7:3)

出典と根拠

ORDレコード
ord-89145b683fe949b1ac2ffea1169a32ad
出典データセット
uspto-grants-2005_07
特許番号
US06914062B2

反応ノート

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