Water → HCID 10193906, compound

HRID 720714Notes

Reaction equation

HRID 720714 reaction equation
C(O[C:4](=[N:6][C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[CH3:5])C.Cl.[NH:20]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH2:31])(=[O:30])=[O:29])=[CH:24][CH:23]=1)[NH2:21].C(N(CC)CC)C.O>ClCCl.CO>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([C:7]2[N:20]([C:22]3[CH:23]=[CH:24][C:25]([S:28]([NH2:31])(=[O:30])=[O:29])=[CH:26][CH:27]=3)[N:21]=[C:4]([CH3:5])[N:6]=2)[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 21894690HCID 21894690, compound

Product 1

HCID 10193906HCID 10193906, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

N-(1-ethoxy-ethylidene)-3,4-dimethoxy-benzamide 536 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 re-crystallized in acetone and hexane phase. As a result, 4-[5-(3,4-dimethoxy-phenyl)-3-mehtyl-[1,2,4]triazole-1-yl]-benzenesulfonamide (575 mg, yield: 72%) 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-bbab680a96f540519fc35a507c657cc8
Source dataset
uspto-grants-2006_11
Patent number
US07135572B2

Reaction notes

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