3,4-Dimethylaniline → 2-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide

HRID 1514922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514922
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[N:13]([CH3:14])[C:12]2[CH:15]=[CH:16][C:17]([C:19](O)=[O:20])=[CH:18][C:11]=2[N:10]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:43][C:44]1[CH:45]=[C:46]([CH:48]=[CH:49][C:50]=1[CH3:51])[NH2:47]>CN(C=O)C.O>[CH3:43][C:44]1[CH:45]=[C:46]([NH:47][C:19]([C:17]2[CH:16]=[CH:15][C:12]3[N:13]([CH3:14])[C:9]([C:3]4[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])=[N:10][C:11]=3[CH:18]=2)=[O:20])[CH:48]=[CH:49][C:50]=1[CH3:51]

Komponenten

7

Edukt 4

HCID 72483,4-DimethylanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 638902812-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid

Produkt 1

HCID 669660132-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 2-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid (100 mg), EDCI (59 mg) and HOBt (42 mg) in DMF (2 mL) was added 3,4-dimethylaniline (38 mg) and the mixture was stirred at room temperature for 18 h. The mixture was poured into water and was extracted with EtOAc. The organic phase was washed with water (3×) and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography using EtOAc/CH2Cl2 (1:5) as eluent to give 2-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide as a glasslike solid; MS (m/z) 424 (M+1); 1H NMR (CDCl3, 400 MHz) δ 8.36 (s, 1H), 8.24 (s, 1H), 8.00 d, J=8.59 Hz, 1H), 7.52-7.39 (m, 6H), 7.10 (d, J=8.08 Hz, 1H), 3.65 (s, 3H), 2.28 (s, 3H), 2.25 (s, 3H).

Aufarbeitung

  1. extractionwas extracted with EtOAc
  2. washThe organic phase was washed with water (3×)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-695f7d0142a54c15afc4e24263478fb7
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

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