Sodium Sulfite → Sodium benzoxazole-2-methanesulfonate

HRID 427088

Reaction equation

HRID 427088 reaction equation
Br[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[S:12]([O-:15])([O-:14])=[O:13].[Na+:16].[Na+]>CO.O>[O:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:3]1[CH2:2][S:12]([O-:15])(=[O:14])=[O:13].[Na+:16]

Participants

5

Reactant 2

HCID 24437Sodium SulfiteHCID 127459442-(Bromomethyl)benzo[d]oxazole

Product 1

HCID 23672978Sodium benzoxazole-2-methanesulfonateYield 135.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3.0 g of 2-bromomethylbenzoxazole [prepared according to the procedures described in Belgian Pat. No. 624,463] in 40 ml of methanol was added a solution of 1.9 g of sodium sulfite in 40 ml of water. The mixture was heated with stirring at 60° C. for 6 hours and concentrated under reduced pressure to give crude sodium benzoxazole-2-methanesulfonate (4.5 g). To the sodium salt was added 15 ml of phosphorus oxychloride and the mixture was heated under reflux for one hour. The removal of the remaining phosphorus oxychloride by distillation under reduced pressure gave the desired product as an oil.

Workup

  1. temperatureThe mixture was heated
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-843070517e574e1dbf381502713159f3
Source dataset
uspto-grants-1979_10
Patent number
US04172896

Linked notes

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