Water → 6-[5-(4-Bromo-phenyl)-3-methyl-[1,2,4]triazole-1-yl]-pyridine-3-sulfonic acid amide

HRID 1376087Notes

Reaction equation

HRID 1376087 reaction equation
C(O[C:4](=[N:6][C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1)[CH3:5])C.[NH:16]([C:18]1[N:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1)[NH2:17].O>ClCCl.CO>[Br:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]2[N:16]([C:18]3[N:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[N:17]=[C:4]([CH3:5])[N:6]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 120965906-Hydrazinylpyridine-3-sulfonamideHCID 21894671N-(1-ethoxy-ethylidene)-4-bromo-benzamide

Product 1

HCID 102160606-[5-(4-Bromo-phenyl)-3-methyl-[1,2,4]triazole-1-yl]-pyridine-3-sulfonic acid amideYield 53%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

N-(1-ethoxy-ethylidene)-4-bromo-benzamide 565 mg (2.09 mmol) was dissolved in a mixed solvent of dichloromethane 20 ml and methanol 10 ml, and 6-hydrazinopyridine-3-sulfonic acid amide 433 mg (2.23 mmol) was added to the solution and stirred for 8 hours. After completing the reaction, water 20 ml was added to the reacting solution and extracted two times with dichloromethane, and then, the collected organic layer was washed with saturated brine. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure, and the resulting product was re-crystallized in acetone and hexane phase. As a result, 6-[5-(4-bromo-phenyl)-3-methyl-[1,2,4]triazole-1-yl]-pyridine-3-sulfonic acid amide (437 mg, yield: 53%) was obtained as a solid phase.

Workup

  1. additionwas added to the solution
  2. additionwas added to the reacting solution
  3. extractionextracted two times with dichloromethane
  4. washthe collected organic layer was washed with saturated brine
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting product was re-crystallized in acetone

Sources & evidence

ORD record
ord-37e1e3c672ff4e11a79cc07989bc6923
Source dataset
uspto-grants-2007_01
Patent number
US07169929B2

Reaction notes

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