3,4-Dimethoxybenzenesulfonyl chloride → 3,4-Dimethoxy-N-(1-methyl-3-phenyl-1,2,4-triazol-5-yl)benzenesulfonamide

HRID 1258618Notes

Reaction equation

HRID 1258618 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[N:5][C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:3]1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([S:24](Cl)(=[O:26])=[O:25])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>N1C=CC=CC=1.CC(O)=O.O>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([S:24]([NH:7][C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:5]=2)(=[O:25])=[O:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

Participants

6

Reactant 2

HCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 125813071-methyl-3-phenyl-1H-1,2,4-triazol-5-amine

Product 1

HCID 249945063,4-Dimethoxy-N-(1-methyl-3-phenyl-1,2,4-triazol-5-yl)benzenesulfonamideYield 19.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 1-methyl-3-phenyl-1,2,4-triazol-5-amine (320 mg, 2 mmol) in 10 mL dry pyridine was added 529 mg (2.23 mmol) of 3,4-dimethoxybenzenesulfonyl chloride. The solution was stirred at room temperature under Argon. After 21 h, the pyridine was removed in vacuo and flashed off with toluene. The salt was partitioned between EtOAc and water. The EtOAc phase was extracted alternately with 1M NaOH and H2O. The basic phase was made acid (pH˜3) with 1M HCl and extracted with EtOAc. The organic phase was evaporated in vacuo, toluene was added and was again evaporated in vacuo to give a white solid. The product was taken up in hot HOAc (16 mL), diluted with H2O (10 mL) and seeded to give 143 mg of white needles with mp 279-280° C. after drying in vacuo.

Workup

  1. customthe pyridine was removed in vacuo
  2. customThe salt was partitioned between EtOAc and water
  3. extractionThe EtOAc phase was extracted alternately with 1M NaOH and H2O
  4. extractionextracted with EtOAc
  5. customThe organic phase was evaporated in vacuo, toluene
  6. additionwas added
  7. customwas again evaporated in vacuo
  8. customto give a white solid

Sources & evidence

ORD record
ord-f4d2cd777fc14e0680f73f22b9f2ff69
Source dataset
uspto-grants-2013_06
Patent number
US08466182B2

Reaction notes

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