4-Toluenesulfonyl chloride → 4-Methyl-N-(1-methyl-3-phenyl-1,2,4-triazol-5-yl)benzenesulfonamide
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][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([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:23])=[O:22])=[CH:17][CH:16]=1Participants
Procedure
To a solution of 1-methyl-3-phenyl-1,2,4-triazol-5-amine (320 mg, 2 mmol) in 10 mL of dry pyridine was added 427 mg of 4-methylbenzenesulfonyl chloride (224 mmol). The solution was stirred at room temperature under Argon. After 23 h, the pyridine was removed in vacuo and flashed off with toluene, and the residue was partitioned between 1M NaOH and EtOAc. The alkaline phase was made acidic and the flocculent solid was collected by filtration and taken up in acetone. The aqueous phase was extracted with EtOAc, washed with H2O and dried over Na2SO4. The acetone and the EtOAc phases were combined and evaporated in vacuo to give 0.15 g of a white solid which was taken up in hot HOAc (7 mL), diluted with water (4 mL), and seeded to give 80 mg of needles with mp 300-302° C.
Workup
- customthe pyridine was removed in vacuo
- customthe residue was partitioned between 1M NaOH and EtOAc
- filtrationthe flocculent solid was collected by filtration
- extractionThe aqueous phase was extracted with EtOAc
- washwashed with H2O
- dry with materialdried over Na2SO4
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-45e67196195c4664ad8f195471137c02
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071631B2
Reaction notes
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