4-Toluenesulfonyl chloride → 1-(p-Toluenesulfonyloxy)-6-vinyl-1,2,3-benzotriazole

HRID 1733704Notes

Reaction equation

HRID 1733704 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[C:8]([CH:11]=[CH2:12])[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.C(N(CC)CC)C.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C1C=CC=CC=1>[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([O:1][N:2]2[C:6]3[CH:7]=[C:8]([CH:11]=[CH2:12])[CH:9]=[CH:10][C:5]=3[N:4]=[N:3]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 233649821-Hydroxy-6-vinyl-1,2,3-benzotriazole

Product 1

HCID 203000121-(p-Toluenesulfonyloxy)-6-vinyl-1,2,3-benzotriazoleYield 64.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
10 °C

Procedure

In dry benzene (300 ml) are dissolved 1-hydroxy-6-vinyl-1,2,3-benzotriazole (4.83 g) and triethylamine (3.2 g) under stirring, and thereto is added dropwise a solution of p-toluenesulfonyl chloride (5.8 g) in benzene (50 ml) under cooling at 10° C. The mixture is stirred at room temperature for 2 hours. The reaction mixture is poured onto ice-water (200 ml) and extracted with ethyl acetate (60 ml, three times). The combined extracts are washed with an aqueous sodium hydrogen carbonate and then water, dried over anhydrous magnesium sulfate, treated with charcoal and then concentrated under a reduced pressure. The resulting residue is recrystallized from ethyl acetate-n-hexane to give colorless crystals of 1-(p-toluenesulfonyloxy)-6-vinyl-1,2,3-benzotriazole (6.1 g), melting point: 90°-91° C. The filtrate is further concentrated, and the resulting residue is recrystallized from benzene-n-hexane to give additionally the desired product (1.9 g).

Workup

  1. stirringThe mixture is stirred at room temperature for 2 hours
  2. additionThe reaction mixture is poured onto ice-water (200 ml)
  3. extractionextracted with ethyl acetate (60 ml, three times)
  4. washThe combined extracts are washed with an aqueous sodium hydrogen carbonate
  5. dry with materialwater, dried over anhydrous magnesium sulfate
  6. additiontreated with charcoal
  7. concentrationconcentrated under a reduced pressure
  8. customThe resulting residue is recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-ec35d24768a1459087011a02aa4cc694
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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