1-Methylimidazole → (2-amino-5-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methanone

HRID 29509

反応式

HRID 29509 の反応式
[Li]CCCC.[CH3:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.[NH2:12][C:13]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:14]=1[C:15](O)=[O:16].[NH4+].[Cl-]>CCCCCC.CCOCC>[NH2:12][C:13]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:14]=1[C:15]([C:8]1[N:7]([CH3:6])[CH:11]=[CH:10][N:9]=1)=[O:16]

参加物

7

反応物 4

HCID 13901-MethylimidazoleHCID 124762-Amino-5-chlorobenzoic acidHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

生成物 1

HCID 10998977(2-amino-5-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methanone収率 13.7%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

実験手順

To a solution of nBuLi (0.0730 mol) in hexane was added N-methyl imidazole (0.0608 mol) drop wise at -40° C. over 30 min under a nitrogen atmosphere. The resulting yellow solution was stirred for a further 3 hr at rt, and then refluxed for 1 h. 2-amino-5-chlorobenzoic acid (1.74 g, 0.01014 mole) in dry ether (60 ml) was then added to the reaction mixture. The reaction mixture was stirred overnight at rt. To the reaction mixture was added saturated NH4Cl solution and the resulting mixture extracted with ethyl acetate (2×150 ml). The combined organic layers were dried over Na2SO4. After removal of solvent, the residue was purified by the flash chromatography using ethyl acetate/hexane (1:4) as eluent. Crystallization of the product from Et2O/hexane mixture gave 300 mg (13.7%) of product as yellow solid.

後処理

  1. temperaturerefluxed for 1 h
  2. stirringThe reaction mixture was stirred overnight at rt
  3. extractionthe resulting mixture extracted with ethyl acetate (2×150 ml)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customAfter removal of solvent
  6. customthe residue was purified by the flash chromatography
  7. customCrystallization of the product from Et2O/hexane mixture

出典と根拠

ORDレコード
ord-435f973cdb9d4431b3d43eeefb9a3641
出典データセット
uspto-grants-2008_09
特許番号
US07420055B2

関連ノート

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