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

HRID 1733684Notes

Reaction equation

HRID 1733684 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.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20].O>C1C=CC=CC=1>[CH3:18][S:19]([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:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl esterYield 84.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
10 °C

Procedure

1-Hydroxy-1,2,3-benzotriazole (648 g) and triethylamine (675 ml) are dissolved in benzene (2,800 ml). To the solution is added dropwise a solution of methanesulfonyl chloride (535 g) in benzene (675 ml) with stirring at a temperature of lower than 10° C. over a period of 2.2 hours. The mixture is stirred at the same temperature for 2.3 hours and allowed to stand overnight. To the reaction mixture is added water (1,000 ml). The benzene layer is separated out. The aqueous layer is extracted twice with ethyl acetate (3,000 ml and 2,000 ml), and the extracts are combined and washed with a saturated aqueous sodium hydrogen carbonate (200 ml×2) and water and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off under a reduced pressure. The resulting crystals are washed with petroleum ether (500 ml) and dried to give faint yellow crystals of 1-methane-sulfonyloxy-1,2,3-benzotriazole (842 g), melting point: 88°-90° C.

Workup

  1. stirringThe mixture is stirred at the same temperature for 2.3 hours
  2. waitto stand overnight
  3. customThe benzene layer is separated out
  4. extractionThe aqueous layer is extracted twice with ethyl acetate (3,000 ml and 2,000 ml)
  5. washwashed with a saturated aqueous sodium hydrogen carbonate (200 ml×2) and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter drying
  8. distillationthe solvent is distilled off under a reduced pressure
  9. washThe resulting crystals are washed with petroleum ether (500 ml)
  10. customdried

Sources & evidence

ORD record
ord-e9746b88715041228863569239ded187
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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