4-Chlorobenzenesulfonyl chloride → 1-(p-Chlorobenzenesulfonyloxy)6-vinyl-1,2,3-benzotriazole

HRID 1733703Notes

Reaction equation

HRID 1733703 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.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C1C=CC=CC=1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([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:29])=[O:28])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 233649821-Hydroxy-6-vinyl-1,2,3-benzotriazole

Product 1

HCID 203000091-(p-Chlorobenzenesulfonyloxy)6-vinyl-1,2,3-benzotriazoleYield 83.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
10 °C

Procedure

In benzene (100 ml) are dissolved 1-hydroxy-6-vinyl-1,2,3-benzotriazole (8.0 g) and triethylamine (5 g) under stirring and thereto is added dropwise a solution of p-chlorobenzenesulfonyl chloride (10.6 g) in benzene (100 ml) under cooling to 10° C. The mixture is stirred at room temperature for 3 hours. The reaction mixture is poured onto ice-water (200 ml) and then extracted with ethyl acetate (150 ml, twice). The combined extracts are washed with water, dried over anhydrous magnesium sulfate, treated with charcoal and then concentrated till about 30 ml. To the mixture is added n-hexane and the mixture is allowed to stand at a cooled place. The precipitated crystals are separated by filtration to give 1-(p-chlorobenzenesulfonyloxy)6-vinyl-1,2,3-benzotriazole (13.9 g), melting point: 125° C. The filtrate is further concentrated and the resulting residue is dissolved in ethyl acetate (10 ml). To the solution is added n-hexane and the mixture is allowed to stand at a cooled place to give additionally the desired product (1.0 g).

Workup

  1. stirringThe mixture is stirred at room temperature for 3 hours
  2. additionThe reaction mixture is poured onto ice-water (200 ml)
  3. extractionextracted with ethyl acetate (150 ml
  4. washThe combined extracts are washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additiontreated with charcoal
  7. concentrationconcentrated till about 30 ml
  8. additionTo the mixture is added n-hexane
  9. customThe precipitated crystals are separated by filtration

Sources & evidence

ORD record
ord-df1bde1845af4be4a480f020f0d4fa32
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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