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

HRID 1169962ノート

反応式

HRID 1169962 の反応式
[CH3:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:12]([N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(#N)C>[CH2:12]([N:19]1[CH:23]=[CH:22][N:21]=[C:20]1[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=1[CH3:1])=[O:6])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 117822,3-Dimethylbenzoic acidHCID 779181-Benzylimidazole

生成物 1

HCID 66771502(1-Benzyl-1H-imidazol-2-yl)(2,3-dimethylphenyl)methanone収率 99.2%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 24386Thionyl Chloride溶媒

実験手順

A solution of 2,3-dimethylbenzoic acid (100 g, 666 mmol) in thionyl chloride (350 ml) was heated at 80° C. for 1 h, before cooling to room temperature and concentrating in vacuo. To the residue was added toluene (100 ml) and the solution was again concentrated in vacuo. The intermediate acid chloride was added to a mixture of 1-benzylimidazole (100 g, 632 mmol) and triethylamine (100 ml) in acetonitrile (1 l) and the reaction mixture was heated at reflux for 18 h. The reaction mixture was concentrated in vacuo and to the residue was added diethyl ether (500 ml) and ethyl acetate (50 ml). This solution was washed with water (500 ml) and saturated aqueous sodium hydrogen carbonate solution (500 ml), filtered through silica gel (100 g) and concentrated in vacuo to give the title compound (182 g).

後処理

  1. concentrationconcentrating in vacuo
  2. additionTo the residue was added toluene (100 ml)
  3. concentrationthe solution was again concentrated in vacuo
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 18 h
  6. concentrationThe reaction mixture was concentrated in vacuo and to the residue
  7. additionwas added diethyl ether (500 ml) and ethyl acetate (50 ml)
  8. washThis solution was washed with water (500 ml) and saturated aqueous sodium hydrogen carbonate solution (500 ml)
  9. filtrationfiltered through silica gel (100 g)
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b237dedd3e4c4c7790ebe0415e1d4398
出典データセット
uspto-grants-2010_11
特許番号
US07825149B2

反応ノート

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