Water → HCID 10308859, compound

HRID 720713Notes

Reaction equation

HRID 720713 reaction equation
C(O[C:4](=[N:6][C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])[CH3:5])C.Cl.[NH:18]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1)[NH2:19].C(N(CC)CC)C.O>ClCCl.CO>[CH3:15][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]1[N:18]([C:20]2[CH:21]=[CH:22][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:24][CH:25]=2)[N:19]=[C:4]([CH3:5])[N:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 21894672HCID 21894672, compound

Product 1

HCID 10308859HCID 10308859, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

N-(1-ethoxy-ethylidene) -2-methoxy-benzamide 462 mg (2.09 mmol) was dissolved in a mixed solvent of dichloromethane 20 ml and methanol 10 ml, and 4-hydrazinobenzenesulfonamide hydrochloride 515 mg (2.23 mmol) was added to the solution. Then, triethylamine 0.35 ml (2.51 mmol) was slowly added dropwise at room temperature for 10 minutes 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 purified through a flash column chromatography (ethyl acetate:normal hexane=7:3). As a result, 4-[5-(2-methoxy-phenyl)-3-methyl-[1,2,4]triazole-1-yl]-benzenesulfonamide (86 mg, yield: 12%) was obtained as a liquid 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 purified through a flash column chromatography (ethyl acetate:normal hexane=7:3)

Sources & evidence

ORD record
ord-d727e97c04124a688a36185030747878
Source dataset
uspto-grants-2006_11
Patent number
US07135572B2

Reaction notes

Loading…