Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → p-Toluenesulfonic acid

HRID 82745Notes

Reaction equation

HRID 82745 reaction equation
NN1C(C)=NN=N1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O-:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1.[NH+]1C=CC=CC=1>C(O)C>[CH3:18][C:8]1[CH:9]=[CH:10][C:11]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 40764305-Methyl-1-aminotetrazole

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-Amino-5-methyltetrazole (71 mg, 0.72 mmol) and pyridinium para-toluenesulfonate (6 mg, 0.024 mmol) were dissolved in absolute ethanol (10 ml) and heated to reflux for 15 minutes. Compound 37(f) (0.17 g, 0.41 mmol) in ethanol (6 ml) was added dropwise to the solution. The reaction was stirred at reflux for 3 hours, and then cooled to room temperature overnight. The solvent was removed in vacuo and diluted with t-butyl methyl ether to provide the tosic acid salt, which was isolated by filtration and dried in vacuo. This solid was treated with sodium bicarbonate (20 rug) in water (6 to 7 ml) and ethyl acetate to form the free base. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organics were dried over MgSO4, filtered, and concentrated by rotary evaporation to provide 0.12 g of the desired product.

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 minutes
  3. temperatureat reflux for 3 hours
  4. customThe solvent was removed in vacuo
  5. additiondiluted with t-butyl methyl ether

Sources & evidence

ORD record
ord-ad2fa63e51204cf58f47ce488a7e391a
Source dataset
uspto-grants-2014_09
Patent number
US08846735B2

Reaction notes

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