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

HRID 1514920

반응식

HRID 1514920 반응식
[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]

참가 물질

7

반응물 4

HCID 962WaterHCID 67372,6-DichlorobenzaldehydeHCID 2733225Ytterbium triflate2회HCID 2824047Ethyl 3-amino-4-(methylamino)benzoate

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a86591ff71ae44ff9e46f9b495c8a473
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222248B2

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