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

HRID 1733683Notes

Reaction equation

HRID 1733683 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.CN(C)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17].O>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:15][S:16]([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:18])=[O:17]

Participants

7

Reactant 4

HCID 962WaterHCID 1146TrimethylamineHCID 31297Methanesulfonyl chlorideHCID 757711-Hydroxybenzotriazole

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Hydroxy-1,2,3-benzotriazole (6.5 g) and trimethylamine (7.0 ml) are dissolved in benzene (50 ml). To the solution is added dropwise methanesulfonyl chloride (3.9 ml) with stirring under ice-cooling and the mixture is stirred for 2 hours and then allowed to stand overnight. To the reaction mixture are added water and ethyl acetate. The ethyl acetate layer is washed with water and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off. The resulting crystals are washed with petroleum ether to give 1-methanesulfonyloxy-1,2,3-benzotriazole (9.2 g), melting point: 90°-92° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred for 2 hours
  3. washThe ethyl acetate layer is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter drying
  6. distillationthe solvent is distilled off
  7. washThe resulting crystals are washed with petroleum ether

Sources & evidence

ORD record
ord-a245e583a757411f8617929bac586d8e
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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