5-Bromo-1-methyl-1H-imidazole → (1-Methyl-1H-imidazol-5-yl)(3-methyl-4-nitrophenyl)methanone

HRID 1507310

反応式

HRID 1507310 の反応式
CC[Mg+].[Br-].Br[C:6]1[N:10]([CH3:11])[CH:9]=[N:8][CH:7]=1.CON(C)[C:15](=[O:26])[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=1>C(Cl)Cl>[CH3:11][N:10]1[C:6]([C:15]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=2)=[O:26])=[CH:7][N:8]=[CH:9]1

参加物

5

反応物 3

HCID 15152585-Bromo-1-methyl-1H-imidazoleHCID 46318653N-methoxy-N,3-dimethyl-4-nitrobenzamideHCID 178461630HCID 178461630、化合物

生成物 1

HCID 86715615(1-Methyl-1H-imidazol-5-yl)(3-methyl-4-nitrophenyl)methanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of EtMgBr (3.0 M in diethylether, 8.5 mL, 25.69 mmol) was added dropwise, over a 25 minute period to a solution of 5-bromo-1-methyl-1H-imidazole (4.1 g, 25.69 mmol) in dry DCM (25 mL). The mixture was stirred at room temperature for 15 minutes, cooled in an ice-brine bath and N-methoxy-N,3-dimethyl-4-nitrobenzamide (4.8 g, 21.41 mmol. Intermediate 13: step a) dissolved in 10 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and the mixture stirred at room temperature for 48 hours. Water was added to the suspension followed by 6 M aqueous HCl slowly to neutralize the mixture (pH=6-7). More DCM was added and the layers were separated. The organic layer was dried over Na2SO4, filtered and concentrated. Et2O was added, the slurry sonicated, and the precipitates filtered to provide the title compound as a tan solid.

後処理

  1. temperaturecooled in an ice-brine bath
  2. additionwas added dropwise
  3. customA dark brown solid mass formed
  4. customThe ice bath was removed
  5. stirringthe mixture stirred at room temperature for 48 hours
  6. additionWater was added to the suspension
  7. additionMore DCM was added
  8. customthe layers were separated
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. additionEt2O was added
  13. customthe slurry sonicated
  14. filtrationthe precipitates filtered

出典と根拠

ORDレコード
ord-841b15bbce4941b98c52ed10e7237997
出典データセット
uspto-grants-2015_12
特許番号
US09221804B2

関連ノート

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