Benzenesulfonyl chloride → HCID 1811360, compound

HRID 1733706Notes

Reaction equation

HRID 1733706 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[N:4][N:3]1[OH:12].C(=O)([O-])O.[Na+].[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O.C(OCC)(=O)C>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[N:4][N:3]1[O:12][S:24]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:26])=[O:25]

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 1811360HCID 1811360, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In water (20 ml) are dissolved 4-oxo-3,4-dihydro-3-hydroxy-1,2,3-benzotriazine (2.4 g) and sodium hydrogen carbonate (1.3 g), and thereto is added a solution of benzenesulfonyl chloride (2.65 g) in ethyl acetate (20 ml) under ice-cooling and the mixture is stirred for 2 hours. The precipitated crystals are separated by filtration. The ethyl acetate layer is separated from the filtrate and concentrated. The resulting crystals are separated by filtration and combined with the crystals obtained above. The crystals are washed with ether, dried and then recrystallized from benzene to give 4-oxo-3,4-dihydro-3-benzene-sulfonyloxy-1,2,3-benzotriazine (4.0 g), melting point: 132°-134° C. Infrared spectrum: 1705, 1390, 1195 cm-1.

Workup

  1. temperaturecooling
  2. customThe precipitated crystals are separated by filtration
  3. customThe ethyl acetate layer is separated from the filtrate
  4. concentrationconcentrated
  5. customThe resulting crystals are separated by filtration
  6. customobtained above
  7. washThe crystals are washed with ether
  8. customdried
  9. customrecrystallized from benzene

Sources & evidence

ORD record
ord-8b7d490f22cd4969ae8a5a653fb72c15
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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