Diethyl Ether → HCID 20031575, compound

HRID 1733700Notes

Reaction equation

HRID 1733700 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.CCOCC.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[OH-].[Na+]>[C:17]1([S:23]([O:1][N:2]2[C:6]3[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=3[N:4]=[N:3]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7369Benzenesulfonyl chlorideHCID 2327116-Chloro-1-hydroxy-1H-benzotriazole

Product 1

HCID 20031575HCID 20031575, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In 1 N aqueous sodium hydroxide (50 ml) is dissolved 1-hydroxy-6-chloro-1,2,3-benzotriazole (4.5 g) and thereto is added ether (10 ml). To the solution is added benzenesulfonyl chloride (6.0 g) with stirring under ice-cooling and the mixture is stirred at the same temperature for 75 minutes. The reaction mixture is filtered to give crystals. The filtrate is extracted with ethyl acetate (150 ml), and the extract is distilled to remove the solvent. The resulting crystals are combined with those obtained above and recrystallized from benzene-n-hexane to give 1-benzenesulfonyloxy-6-chloro-1,2,3-benzotriazole (6.0 g), melting point: 110°-110.5° C. Infrared spectrum (Nujor): 1200, 1086 cm-1.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at the same temperature for 75 minutes
  3. filtrationThe reaction mixture is filtered
  4. customto give crystals
  5. extractionThe filtrate is extracted with ethyl acetate (150 ml)
  6. distillationthe extract is distilled
  7. customto remove the solvent
  8. customthose obtained above and
  9. customrecrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-a15e78ee9527406c9d90a9378732404a
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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