Water → 2-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid ethyl ester

HRID 1514920

反応式

HRID 1514920 の反応式
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH3:12])=[C:7]([NH2:13])[CH:6]=1)[CH3:2].[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:17]=1[CH:18]=O.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].O>CS(C)=O.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]2[N:11]([CH3:12])[C:18]([C:17]3[C:16]([Cl:15])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:24])=[N:13][C:7]=2[CH:6]=1)=[O:14])[CH3:2]

参加物

7

反応物 4

HCID 962WaterHCID 67372,6-DichlorobenzaldehydeHCID 2733225Ytterbium triflate2 回HCID 2824047Ethyl 3-amino-4-(methylamino)benzoate

生成物 1

HCID 669657182-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3-amino-4-methylaminobenzoic acid ethyl ester (388 mg) and 2,6-dichlorobenzaldehyde (350 mg) in DMSO (4 mL) was added Yb(OTf)3 (50 mg) and the solution was stirred at room temperature for 24 h. More Yb(OTf)3 was added and stirring was continued for 24 h. This process was repeated another two times. The reaction mixture was partioned between water and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated. The residue was purified by flash chromatography using a gradient of ethyl acetate/CH2Cl2 (0% to 25%) to give 2-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid ethyl ester as a beige solid, mp=164-166° C.; MS (m/z) 349 (M+1).

後処理

  1. stirringstirring
  2. waitwas continued for 24 h
  3. extractionThe aqueous layer was extracted with EtOAc
  4. customThe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-a86591ff71ae44ff9e46f9b495c8a473
出典データセット
uspto-grants-2012_07
特許番号
US08222248B2

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