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

HRID 1514891ノート

反応式

HRID 1514891 の反応式
[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]

参加物

5

反応物 3

HCID 342242,3-DimethylbenzaldehydeHCID 2733225Ytterbium triflate2 回HCID 66965643HCID 66965643、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-08438196a75346849b3592f7ba6cd598
出典データセット
uspto-grants-2012_07
特許番号
US08222248B2

反応ノート

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