Sodium Sulfite → 1,2-Benzisoxazole-3-methanesulfonate sodium

HRID 427087Notes

Reaction equation

HRID 427087 reaction equation
Br[CH2:2][C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][N:4]=1.[S:12]([O-:15])([O-:14])=[O:13].[Na+:16].[Na+]>CO.O>[O:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:3]([CH2:2][S:12]([O-:15])(=[O:14])=[O:13])=[N:4]1.[Na+:16]

Participants

5

Reactant 2

HCID 24437Sodium SulfiteHCID 34991891,2-Benzisoxazole, 3-(bromomethyl)-

Product 1

HCID 236749341,2-Benzisoxazole-3-methanesulfonate sodium

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8.0 of 3-bromomethyl-1,2-benzisoxazole (m.p. 64°-66° C.) in 130 ml of methanol was added a solution of 8.1 g of sodium sulfite in 130 ml of water. The mixture was heated with stirring at 50° C. for 4 hours and concentrated under reduced pressure. The crystalline residue was dissolved in 250 ml of methanol with warming and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure and the crystalline residue was washed with diethyl ether to give crude sodium 1,2-benzisoxazole-3-methanesulfonate (10.5 g).

Workup

  1. temperatureThe mixture was heated
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crystalline residue was dissolved in 250 ml of methanol
  4. temperaturewith warming
  5. filtrationthe insoluble material was filtered off
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. washthe crystalline residue was washed with diethyl ether

Sources & evidence

ORD record
ord-4386bd42a4e84c10953765be27bc669c
Source dataset
uspto-grants-1979_10
Patent number
US04172896

Reaction notes

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