2,3-Dimethylbenzaldehyde → 2-(2,3-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide

HRID 1514891노트

반응식

HRID 1514891 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[NH2:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=1)=[O:6].[CH3:20][C:21]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=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]>CS(C)=O>[CH3:15][C:10]1[CH:9]=[C:8]([NH:7][C:5]([C:4]2[CH:16]=[CH:17][C:18]3[N:19]=[C:23]([C:22]4[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:21]=4[CH3:20])[NH:1][C:2]=3[CH:3]=2)=[O:6])[CH:13]=[CH:12][C:11]=1[CH3:14]

참가 물질

5

반응물 3

HCID 342242,3-DimethylbenzaldehydeHCID 2733225Ytterbium triflate2회HCID 66965643HCID 66965643, 화합물

생성물 1

HCID 669661432-(2,3-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 3,4-diamino-N-(3,4-dimethylphenyl)-benzamide (71 mg) and 2,3-dimethylbenzaldehyde (34 mg) in DMSO (1 mL) was added Yb(OTf)3 and the mixture was stirred at room temperature for 4 h. Additional Yb(OTf)3 was added and stirring was continued until starting material was consumed. Water was added and the mixture was extracted with EtOAc. The organic phase was washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using CH2Cl2/EtOAc (2:1) as eluent to furnish 2-(2,3-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide as a beige solid, MS (m/z) 370 (M−1).

후처리

  1. stirringstirring
  2. customwas consumed
  3. additionWater was added
  4. extractionthe mixture was extracted with EtOAc
  5. washThe organic phase was washed with water
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-08438196a75346849b3592f7ba6cd598
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222248B2

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