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

HRID 734471노트

반응식

HRID 734471 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5a22b26a7f354c30a866bb816d169569
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592362B2

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