Triethylamine → (1-Benzyl-1H-imidazol-2-yl)(2,3-dimethylphenyl)methanone

HRID 734471ノート

反応式

HRID 734471 の反応式
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:20][C:21]1[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>ClCCl.O>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:23]([C:22]1[CH:26]=[CH:27][CH:28]=[C:29]([CH3:30])[C:21]=1[CH3:20])=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 779181-BenzylimidazoleHCID 28008992,3-Dimethylbenzoyl chloride

生成物 1

HCID 66771502(1-Benzyl-1H-imidazol-2-yl)(2,3-dimethylphenyl)methanone収率 91.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 1-benzyl-1H-imidazole (1.69 Kg, 10.56 mol) in dichloromethane (14.0 L), at −7° C., was added triethylamine (1.61 kg, 10.56 mol). A solution of 2,3-dimethylbenzoyl chloride (2.0 kg, 11.99 mol) in dichloromethane (6.0 L) was then added dropwise and the reaction mixture was stirred at room temperature for 16 h. The reaction was monitored by Thin layer Chromatography. After completion of the reaction, the reaction mixture was diluted with water (5.0 L) and the mixture was stirred for a further 15 min. The two layers were separated and the organic phase was concentrated in vacuo. To the residue was added toluene (8.0 L) and the solution was cooled to −5° C., before addition of hydrochloric acid (5N, 8.0 L). The two layers were separated and the aqueous layer was adjusted to pH 9-12, by addition of aqueous sodium hydroxide solution (50%), and extracted with toluene (4.0 L and then 8.0 L). The combined organic phases were concentrated in vacuo to give the title compound (2.8 kg).

後処理

  1. customAfter completion of the reaction
  2. stirringthe mixture was stirred for a further 15 min
  3. customThe two layers were separated
  4. concentrationthe organic phase was concentrated in vacuo
  5. additionTo the residue was added toluene (8.0 L)
  6. temperaturethe solution was cooled to −5° C., before addition of hydrochloric acid (5N, 8.0 L)
  7. customThe two layers were separated
  8. additionthe aqueous layer was adjusted to pH 9-12, by addition of aqueous sodium hydroxide solution (50%)
  9. extractionextracted with toluene (4.0 L
  10. concentrationThe combined organic phases were concentrated in vacuo

出典と根拠

ORDレコード
ord-5a22b26a7f354c30a866bb816d169569
出典データセット
uspto-grants-2009_09
特許番号
US07592362B2

反応ノート

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