Diethyl Ether → HCID 20300041, compound

HRID 1733690Notes

Reaction equation

HRID 1733690 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.CCOCC.[CH2:16]([S:23](Cl)(=[O:25])=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[OH-].[Na+]>[CH2:16]([S:23]([O:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1)(=[O:25])=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 74740Phenylmethanesulfonyl chlorideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 20300041HCID 20300041, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In 1 N aqueous sodium hydroxide (50 ml) is dissolved 1-hydroxy-1,2,3-benzotriazole (5 g) and thereto is added ether (25 ml). To the solution is added benzylsulfonyl chloride (8 g) with stirring under ice-cooling. The mixture is stirred at the same temperature for 3 hours. The reaction mixture is extracted with ethyl acetate. The extract is washed with a saturated aqueous sodium hydrogen carbonate and water in order and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off and the oily residue is allowed to stand. The resulting crystals are recrystallized from benzene-petroleum ether to give 1-benzylsulfonyloxy-1,2,3-benzotriazole (5.0 g), melting point: 65°-67° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at the same temperature for 3 hours
  3. extractionThe reaction mixture is extracted with ethyl acetate
  4. washThe extract is washed with a saturated aqueous sodium hydrogen carbonate and water in order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter drying
  7. distillationthe solvent is distilled off
  8. customThe resulting crystals are recrystallized from benzene-petroleum ether

Sources & evidence

ORD record
ord-ca4540de887b455dbe93887b30e36ce7
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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