4-Toluenesulfonyl chloride → HCID 178427424, compound

HRID 1258614Notes

Reaction equation

HRID 1258614 reaction equation
[C:1]1([C:7]2[NH:8][C:9]([NH2:12])=[N:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.CCOC(C)=O>N1C=CC=CC=1.CCCCCC>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:12][C:9]2[NH:10][N:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 178509136HCID 178509136, compound

Product 1

HCID 178427424HCID 178427424, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8058HexaneSolvent

Procedure

To a solution of 5-phenyl-4H-1,2,4-triazol-3-amine (354 mg, 2 mmol) in dry pyridine (10 mL) was added 4-methylbenzenesulfonyl chloride (427 mg, 2.24 mmol). The solution was stirred at room temperature under Argon. After 48 h, the pyridine was removed in vacuo and flashed off with toluene. The residue was partitioned between CH2Cl2 and 1M NaOH. The organic phase was washed with 1M NaOH until no turbidity was observed on rectification of a small sample. The alkaline phase was made acidic (˜pH 3) with 1M HCl and extracted with CH2Cl2. After drying over Na2SO4, the solvent was removed in vacuo to give 0.41 g crude product. The crude product was dissolved hot EtOAc (16 mL), diluted with hexane (16 mL), and seeded to give fine white needles (304 mg) with mp 220-221° C.

Workup

  1. customthe pyridine was removed in vacuo
  2. customThe residue was partitioned between CH2Cl2 and 1M NaOH
  3. washThe organic phase was washed with 1M NaOH until no turbidity
  4. extractionextracted with CH2Cl2
  5. dry with materialAfter drying over Na2SO4
  6. customthe solvent was removed in vacuo
  7. customto give 0.41 g crude product

Sources & evidence

ORD record
ord-c543363ad7c64c48959c5c36b8c204be
Source dataset
uspto-grants-2013_06
Patent number
US08466182B2

Reaction notes

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