4,5-Dimethyl-1,2-phenylenediamine → HCID 135506541, compound

HRID 2182346Notes

Reaction equation

HRID 2182346 reaction equation
[Br:1][C:2]1[CH:6]=[N:5][NH:4][C:3]=1[CH:7]=O.[CH3:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([NH2:17])=[C:12]([NH2:18])[CH:11]=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(O)C>[Br:1][C:2]1[CH:6]=[N:5][NH:4][C:3]=1[C:7]1[NH:18][C:12]2[CH:11]=[C:10]([CH3:9])[C:15]([CH3:16])=[CH:14][C:13]=2[N:17]=1

Participants

5

Reactant 3

HCID 766354,5-Dimethyl-1,2-phenylenediamineHCID 656671Sodium PyrosulfiteHCID 27821544-bromo-1H-pyrazole-5-carbaldehyde

Product 1

HCID 135506541HCID 135506541, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Starting with 100 mg of commercial 4-bromo-2H-pyrazole-3-carboxaldehyde, 77.8 mg of 4,5-dimethyl-1,2-phenylenediamine, and 108.6 mg of sodium metabisulphite, in 1 ml of ethanol and 2 ml of dimethylformamide, and after purification by SPE (SCX phase, washing with methanol, extraction with 2N ammoniacal methanol) followed by a chromatography under pressure on silica, 143.2 mg of 2-(4-bromo-2H-pyrazol-3-yl)-5,6-dimethyl-1H-benzimidazole are obtained in the form of a yellow foam.

Workup

  1. custom2 ml of dimethylformamide, and after purification
  2. washby SPE (SCX phase, washing with methanol, extraction with 2N ammoniacal methanol)
  3. customare obtained in the form of a yellow foam

Sources & evidence

ORD record
ord-9fcf8b69f7b0414a96da186ba9e8ca41
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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