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

HRID 1733685Notes

Reaction equation

HRID 1733685 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.O.[OH-].[Na+].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(OCC)(=O)C>[CH3:14][S:15]([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:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-Hydroxy-1,2,3-benzotriazole (25.7 g) is suspended into water (50 ml) and thereto is added 1 N aqueous sodium hydroxide (180 ml). To the resulting solution is added dropwise methanesulfonyl chloride (14.0 ml) with stirring under ice-cooling and thereto is further added ethyl acetate (30 ml), and the mixture is stirred for 4 hours. The reaction mixture is extracted with ethyl acetate, and the extract is washed with water and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off and to the resulting residue is added petroleum ether, and the residue is cracked, filtered and dried to give 1-methanesulfonyloxy-1,2,3-benzotriazole (39.1 g), melting point: 88°-91° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred for 4 hours
  3. extractionThe reaction mixture is extracted with ethyl acetate
  4. washthe extract is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter drying
  7. distillationthe solvent is distilled off and to the resulting residue
  8. additionis added petroleum ether
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-373c27c4570648709a8e7d39f2d185e4
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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