Methanesulfonic Acid → Methanesulfonic acid, 1H-benzotriazol-1-yl ester

HRID 1733692Notes

Reaction equation

HRID 1733692 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.[CH3:11][S:12](O)(=[O:14])=[O:13].C(N(CC)CC)C.S(Cl)(Cl)=O>ClCCl>[CH3:11][S:12]([O:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1)(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl esterYield 28.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (20 ml) are added 1-hydroxy-1,2,3-benzotriazole (2.70 g) and methanesulfonic acid (1.92 g) and thereto is added triethylamine (5.6 ml). To the solution is added dropwise thionyl chloride (1.43 ml) with stirring under ice-cooling during 15 minutes. The mixture is stirred at the same temperature for 1 hour and 10 minutes and at room temperature for 7 hours and 45 minutes, and then allowed to stand overnight. Dichloromethane is distilled off under a reduced pressure. To the residue are added water (30 ml) and ethyl acetate (100 ml). The ethyl acetate layer is washed with a saturated aqueous sodium hydrogen carbonate and water in order and dried over anhydrous sodium sulfate. After drying, the solvent is distilled off. To the residue is added petroleum ether and the mixture is filtered to give 1-methanesulfonyloxy-1,2,3-benzotriazole (1.2 g).

Workup

  1. temperaturecooling during 15 minutes
  2. stirringThe mixture is stirred at the same temperature for 1 hour and 10 minutes and at room temperature for 7 hours and 45 minutes
  3. distillationDichloromethane is distilled off under a reduced pressure
  4. additionTo the residue are added water (30 ml) and ethyl acetate (100 ml)
  5. washThe ethyl acetate layer is washed with a saturated aqueous sodium hydrogen carbonate and water in order
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter drying
  8. distillationthe solvent is distilled off
  9. additionTo the residue is added petroleum ether
  10. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-6a6b6d27e7ef43478587bc8b80d6e345
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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