Chlorzoxazone → 5-Chloro-2-oxobenzoxazoline-6-sulphonyl chloride

HRID 1594626Notes

Reaction equation

HRID 1594626 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.[Cl:12][S:13](O)(=[O:15])=[O:14]>O>[Cl:1][C:2]1[C:3]([S:13]([Cl:12])(=[O:15])=[O:14])=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 2733ChlorzoxazoneHCID 24638Chlorosulfonic acid

Product 1

HCID 798535-Chloro-2-oxobenzoxazoline-6-sulphonyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Chloro-3H-benzooxazol-2-one (10.0 g, 59 mmol) was added in portions to chlorosulfonic acid (30 mL) at −20° C. with stirring. The mixture was stirred at room temperature for 2.5 hours and at 70° C. for 1.5 hours. The cooled reaction mixture was poured slowly into iced-water (300 mL) and stirred for 1 hour. The precipitate was collected and washed with water. The dried precipitate was stirred in chloroform (500 mL) for 3 hours at room temperature, filtered off and dried to give 12.3 g of a pale pink solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 2.5 hours and at 70° C. for 1.5 hours
  2. customThe cooled reaction mixture
  3. stirringstirred for 1 hour
  4. customThe precipitate was collected
  5. washwashed with water
  6. stirringThe dried precipitate was stirred in chloroform (500 mL) for 3 hours at room temperature
  7. filtrationfiltered off
  8. customdried

Sources & evidence

ORD record
ord-705dda679997488c9e4ec13f5eaf7959
Source dataset
uspto-grants-2001_09
Patent number
US06284774B1

Reaction notes

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