Potassium Carbonate → HCID 20300026, compound

HRID 1733687Notes

Reaction equation

HRID 1733687 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([OH:10])(=[O:9])=[O:8])[CH:2]=1.P(Cl)(Cl)(Cl)(Cl)Cl.O[N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[N:19]1.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+]>CCOCC.O.C1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([O:10][N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]=[N:19]2)(=[O:9])=[O:8])[CH:2]=1

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 20300026HCID 20300026, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
150 °C

Procedure

To pyridine-3-sulfonic acid (6 g) is added powdery phosphorus pentachloride (15.8 g) and the mixture is heated at 150° C. for 3 hours. The reaction mixture is concentrated under a reduced pressure at 60° to 70° C. and thereto is added anhydrous xylene. The mixture is concentrated under a reduced pressure and thereto is further added anhydrous xylene, and the mixture is again concentrated. To the resulting residue is gradually added water (20 ml) under cooling with dry ice-acetone to give a solution. The solution is added dropwise to a mixture of 1-hydroxy-1,2,3-benzotriazole (8.3 g), potassium carbonate (8.3 g), water (24 ml), benzene (40 ml) and ether (15 ml) at -2° to 0° C. with stirring. After the addition, to the mixture are added water (18 ml) and ether (15 ml) and the mixture is stirred at room temperature. The mixture is regulated at pH 7 to 8 with 1 N aqueous potassium hydroxide and then stirred for 2 hours. The reaction mixture is extracted with benzene-ether (240 ml). The extract is washed with a saturated aqueous sodium hydrogen carbonate and dried over potassium carbonate. After drying, the solvent is distilled off to give 1-(3-pyridylsulfonyloxy)-1,2,3-benzotriazole (7.2 g; 70%), melting point: 98° C.

Workup

  1. concentrationThe reaction mixture is concentrated under a reduced pressure at 60° to 70° C.
  2. additionis added anhydrous xylene
  3. concentrationThe mixture is concentrated under a reduced pressure
  4. concentrationthe mixture is again concentrated
  5. temperatureunder cooling with dry ice-acetone
  6. customto give a solution
  7. additionAfter the addition
  8. stirringthe mixture is stirred at room temperature
  9. stirringstirred for 2 hours
  10. extractionThe reaction mixture is extracted with benzene-ether (240 ml)
  11. washThe extract is washed with a saturated aqueous sodium hydrogen carbonate
  12. dry with materialdried over potassium carbonate
  13. customAfter drying
  14. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-a8e70e350fe24529820616c224ac18ec
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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