Dimethyl Sulfoxide → toluene-4-sulfonic acid 4-[6-(3,4-dimethyl-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethyl-phenyl ester

HRID 1514880Notes

Reaction equation

HRID 1514880 reaction equation
[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[CH:28]=[C:27]([O:29]CC(=O)N2CCCC2)[CH:26]=[C:25]([CH3:38])[C:22]=1[CH:23]=O.[OH2:39].C[S:41]([CH3:43])=[O:42]>>[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[C:25]([CH3:38])=[CH:26][C:27]([O:29][S:41]([C:43]5[CH:17]=[CH:16][C:4]([CH3:5])=[CH:3][CH:2]=5)(=[O:39])=[O:42])=[CH:28][C:21]=4[CH3:20])[NH:1][C:2]=3[CH:3]=2)=[O:6])[CH:13]=[CH:12][C:11]=1[CH3:14]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 66965643HCID 66965643, compoundHCID 866512572,6-Dimethyl-4-(2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzaldehyde

Product 1

HCID 86651258toluene-4-sulfonic acid 4-[6-(3,4-dimethyl-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethyl-phenyl ester

Procedure

To a solution of 3,4-diamino-N-(3,4-dimethyl-phenyl)-benzamide (102 mg) in DMSO (2 mL) were added 2,6-dimethyl-4-(2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzaldehyde (116 mg) and FeCl3 (1.2 mL in 0.02M THF solution). The mixture was stirred in open air at ambient temperature overnight. The mixture was then diluted by water and extracted with EtOAc. The extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, EtOAc:Hexane=20:80 to 80:10) to give toluene-4-sulfonic acid 4-[6-(3,4-dimethyl-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethyl-phenyl ester: MS (m/z) 540 (M+1).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (SiO2, EtOAc:Hexane=20:80 to 80:10)

Sources & evidence

ORD record
ord-2b8a05fa91534d4ea23c603c5e333622
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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