4,5-Dimethyl-1,2-phenylenediamine → HCID 178422275, compound

HRID 2064583Notes

Reaction equation

HRID 2064583 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:11]=O)[NH:9][N:10]=1.[CH3:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([NH2:21])=[C:16]([NH2:22])[CH:15]=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(O)C>[CH3:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]2[NH:21][C:11]([C:8]3[NH:9][N:10]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[CH:7]=3)=[N:22][C:16]=2[CH:15]=1

Participants

5

Reactant 3

HCID 766354,5-Dimethyl-1,2-phenylenediamineHCID 656671Sodium PyrosulfiteHCID 22477718HCID 22477718, compound

Product 1

HCID 178422275HCID 178422275, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Starting with 16.2 mg of 5-thiophen-2-yl-2H-pyrazole-3-carboxaldehyde, 12.4 mg of 4,5-dimethyl-1,2-phenylenediamine, and 17.3 mg of sodium metabisulphite, in 0.2 ml of ethanol and 0.6 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 and a purification by LC-MS, 5,6-dimethyl-2-(5-thiophen-2-yl-2H-pyrazol-3-yl)-1H-benzimidazole is obtained in the form of a white powder.

Workup

  1. custom0.6 ml of dimethylformamide, and after purification
  2. washby SPE (SCX phase, washing with methanol, extraction with 2N ammoniacal methanol)
  3. customa purification by LC-MS

Sources & evidence

ORD record
ord-5d9ad1e9e6c7442cbc4adcd4e6fb8e17
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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