2,6-Dimethylbenzaldehyde → HCID 66965797, compound

HRID 1514864Notes

Reaction equation

HRID 1514864 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]=[C:24]([CH3:28])[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:22]([C:21]4[C:24]([CH3:28])=[CH:25][CH:26]=[CH:27][C:20]=4[CH3:19])[NH:1][C:2]=3[CH:3]=2)=[O:6])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 5838412,6-Dimethylbenzaldehyde2×HCID 66965669HCID 66965669, compound

Product 1

HCID 66965797HCID 66965797, 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), 2,6-dimethyl-benzaldehyde (0.1 mL in 0.2 M toluene solution) and YB(SO3CF3)3 (0.1 mL in 0.02M THF solution) was shaked at room temperature for 16 h. Then another 0.04 mL of 2,6-dimethyl benzaldehyde (0.2 M) toluene solution was added. The mixture 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 of 2-(2,6-dimethyl-phenyl)-3H-benzoimidazole-5-carboxylic acid (3-chloro-phenyl)-amide as white powder: MS (m/z) 376 (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-a3e5d80eb6d344928bbcbeaee84d8290
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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