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

HRID 29509

반응식

HRID 29509 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-435f973cdb9d4431b3d43eeefb9a3641
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420055B2

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