2-Methylbenzaldehyde → HCID 66965863, compound

HRID 1514865Notes

Reaction equation

HRID 1514865 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[NH2:18])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=1)=[O:6].[CH3:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O>CO>[Cl:14][C:10]1[CH:9]=[C:8]([NH:7][C:5]([C:4]2[CH:15]=[CH:16][C:17]3[N:18]=[C:19]([C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=4[CH3:22])[NH:1][C:2]=3[CH:3]=2)=[O:6])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 107222-MethylbenzaldehydeHCID 66965669HCID 66965669, compound

Product 1

HCID 66965863HCID 66965863, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3,4-diamino-N-(3-chloro-phenyl)-benzamide (0.1 mL in 0.2 M DMSO solution), 2-methyl benzaldehyde (0.1 mL in 0.2 M toluene solution) and FeCl3 (0.05 mL in 0.02M THF solution) was stirred in open air at ambient temperature overnight. The mixture was then diluted by MeOH and the whole was loaded onto a solid phase extraction (SPE) cartridge that contained strong cation exchange (SCX) (1 g media in 6 mL cartridge, United Chemical Technology). Wash-to-waste (5 mL MeOH) was followed by elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N) and, after evaporation of volatiles, the crude was further purified by silica gel column chromatography to give 2-o-tolyl-3H-benzoimidazole-5-carboxylic acid (3-chloro-phenyl)-amide as white powder: MS (m/z) 362 (M+1).

Workup

  1. extractionthe whole was loaded onto a solid phase extraction (SPE) cartridge that
  2. washWash-to-waste (5 mL MeOH)
  3. customby elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N)
  4. customafter evaporation of volatiles
  5. customthe crude was further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c9e12b3ad52f4cedb266ca8fc07f54a3
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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