Benzoic Acid → 1-(Benzoyloxy)-1H-1,2,3-benzotriazole

HRID 1733671Notes

Reaction equation

HRID 1733671 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC1C=CC(S(O[N:28]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[N:30]=[N:29]2)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[C:1]([O:9][N:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=[N:29]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 203000021-(p-Chlorobenzenesulfonyloxy)-1,2,3-benzotriazole

Product 1

HCID 5552441-(Benzoyloxy)-1H-1,2,3-benzotriazoleYield 81.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Benzoic acid (2.44 g) is dissolved in chloroform (30 ml), and thereto are added triethylamine (2.80 ml) under ice-cooling and further 1-(p-chlorobenzenesulfonyloxy)-1,2,3-benzotriazole (6.2 g) at room temperature, and the mixture is stirred for 2 hours. After the reaction, chloroform is distilled off, and to the resulting residue are added water and ethyl acetate. The ethyl acetate layer is washed with water, an aqueous sodium hydrogen sulfate and water in order and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off to give yellow crystals of 1-benzoyloxy-1,2,3-benzotriazole (3.9 g). The product is recrystallized from isopropanol to give faint yellow crystals of the product, melting point: 75°-78.5° C.

Workup

  1. temperaturecooling
  2. distillationis distilled off
  3. additionto the resulting residue are added water and ethyl acetate
  4. washThe ethyl acetate layer is washed with water
  5. dry with materialan aqueous sodium hydrogen sulfate and water in order and dried over anhydrous magnesium sulfate
  6. customAfter drying
  7. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-2083de36b3bc4672b2ac2bba248ffa24
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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