Water → 319474-36-7

HRID 1862168Notes

Reaction equation

HRID 1862168 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[NH:5][N:4]=1)=O.[C:15]1([NH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21].[S].O>CN(C=O)C>[NH:21]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:22]=[C:1]1[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[NH:5][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7243O-PhenylenediamineHCID 5362487SulfurHCID 178520043HCID 178520043, compound

Product 1

HCID 135839310319474-36-7Yield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-formyl-1H-indazole-6-carboxylic acid (2.35 g, 12.42 mmol) in DMF (60 mL) was added 1,2-phenylenediamine (12.42 mmol, 1.34 g) and sulfur powder (1.1 eq, 13.66 mmol). This mixture was then heated to reflux for 6 hours. The reaction was followed by TLC and LC-MS. After cooling, water (50 mL) was added to the reaction and the brown precipitate which formed was filtered and collected to provide 3.1 g (90%) of 3-(1H-benzoimidazol-2-yl)-1H-indazole-6-carboxylic acid. 1H NMR (DMSO-d6) δ 14.01 (1H, s), 8.58 (1H, d, J=8.5 Hz), 8.24 (1H, s), 7.87 (1H, d, J=8.7 Hz), 7.64 (2H, m), 7.25 (2H, m). MS (APCI positive) 279.

Workup

  1. temperatureThis mixture was then heated
  2. temperatureto reflux for 6 hours
  3. temperatureAfter cooling
  4. customthe brown precipitate which formed
  5. filtrationwas filtered
  6. customcollected

Sources & evidence

ORD record
ord-3a5ea7c02ea24a63b70121190672bd5d
Source dataset
uspto-grants-2003_03
Patent number
US06534524B1

Reaction notes

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