Benzoic Acid → 1-Benzoyloxy-6-chloro-1,2,3-benzotriazole

HRID 1733673Notes

Reaction equation

HRID 1733673 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]=[C:34]([Cl:37])[CH:35]=[CH:36][C:31]=3[N:30]=[N:29]2)(=O)=O)=CC=1>ClCCl>[C:1]([O:9][N:28]1[C:32]2[CH:33]=[C:34]([Cl:37])[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 122228411-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole

Product 1

HCID 122228421-Benzoyloxy-6-chloro-1,2,3-benzotriazoleYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzoic acid (2.4 g) is dissolved in dichloromethane (30 ml), and thereto are added triethylamine (2.8 ml) and further 1-(p-chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole (6.9 g) and the mixture is stirred for 4 hours. After the reaction, dichloromethane 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 carbonate and water in order, dried over anhydrous magnesium sulfate and the solvent is distilled off to give white crystals of 1-benzoyloxy-6-chloro-1,2,3-benzotriazole (4.55 g). The product is recrystallized from ethanol to give pure product, melting point: 132° C.

Workup

  1. distillationis distilled off and to the resulting residue
  2. additionare added water and ethyl acetate
  3. washThe ethyl acetate layer is washed with water
  4. dry with materialan aqueous sodium hydrogen carbonate and water in order, dried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-f502517b00264defb7bc283a2a94a3ec
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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