4,5-Dimethyl-1,2-phenylenediamine → HCID 135463035, compound

HRID 2182339Notes

Reaction equation

HRID 2182339 reaction equation
S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH:19]=O)=[N:11]1.[CH3:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([NH2:29])=[C:24]([NH2:30])[CH:23]=1>CN(C)C=O>[CH3:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]2[NH:29][C:19]([C:12]3[C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[NH:10][N:11]=3)=[N:30][C:24]=2[CH:23]=1

Participants

5

Reactant 3

HCID 766354,5-Dimethyl-1,2-phenylenediamineHCID 656671Sodium PyrosulfiteHCID 178520025HCID 178520025, compound

Product 1

HCID 135463035HCID 135463035, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

389 mg of sodium metabisulphite are added, at a temperature in the region of 20° C., to a solution of 300 mg of 1H-indazole-3-carboxaldehyde and 279 mg of 4,5-dimethyl-1,2-phenylenediamine in 3 ml of dimethylformamide. The reaction mixture is refluxed for 4 hours and then cooled to a temperature in the region of 20° C. and filtered through paper. The collected filtrate is concentrated under reduced pressure. The brown lacquer obtained (340 mg) is purified by preparative LC-MS. 138.8 mg of 5,6-dimethyl-2-(1H-indazol-3-yl)-1H-benzimidazole are thus obtained in the form of a beige-coloured powder.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. filtrationfiltered through paper
  3. concentrationThe collected filtrate is concentrated under reduced pressure
  4. customThe brown lacquer obtained (340 mg)
  5. customis purified by preparative LC-MS

Sources & evidence

ORD record
ord-267387cdc261495cb6a03b7a20333183
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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