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

HRID 2064584Notes

Reaction equation

HRID 2064584 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-2737ab3da3814fd5aec26b8a30414950
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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