Imidazole → 2-(2,4-dichlorobenzyloxy)-alpha-(1-imidazolyl)benzaldehyde O-methyloxime

HRID 1489383ノート

反応式

HRID 1489383 の反応式
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH3:8][O:9][N:10]=[C:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27].CCOCC>CN(C=O)C>[CH3:8][O:9][N:10]=[C:11]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27]

参加物

6

反応物 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 53754588alpha-chloro-2-(2,4-dichlorobenzyloxy)benzaldehyde O-methyloxime

生成物 1

HCID 542129432-(2,4-dichlorobenzyloxy)-alpha-(1-imidazolyl)benzaldehyde O-methyloxime収率 48.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Imidazole (2.04 g) was dissolved in DMF (30 ml), and 60% sodium hydride (1.20 g) was added. The mixture was stirred at room temperature for 10 minutes, then α-chloro-2-(2,4-dichlorobenzyloxy)benzaldehyde O-methyloxime (5.17 g) was added, and the mixture was stirred at 120° C. for 2 hours. After completion of the reaction, ether (200 ml) was added, and the mixture was washed with brine (200 ml) twice, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography and recrystallized from ethyl acetate/n-hexane to give 2-(2,4-dichlorobenzyloxy)-α-(1-imidazolyl)benzaldehyde O-methyloxime (2.74 g) as colorless crystals. mp. 122°-123° C.

後処理

  1. stirringthe mixture was stirred at 120° C. for 2 hours
  2. additionwas added
  3. washthe mixture was washed with brine (200 ml) twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product was purified by silica gel chromatography
  7. customrecrystallized from ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-1d27698525d348df9e7f139190ce8563
出典データセット
uspto-grants-1997_10
特許番号
US05677465

反応ノート

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