Chlorzoxazone → HCID 53438971, compound

HRID 858159Notes

Reaction equation

HRID 858159 reaction equation
[CH:1]1[C:6]([Cl:7])=[CH:5][C:4]2[NH:8][C:9]([O:11][C:3]=2[CH:2]=1)=[O:10].Cl[S:13]([OH:16])(=[O:15])=[O:14]>C(Cl)Cl>[Cl:7][C:6]1[C:1]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:2][C:3]2[O:11][C:9](=[O:10])[NH:8][C:4]=2[CH:5]=1

Participants

4

Reactant 2

HCID 2733ChlorzoxazoneHCID 24638Chlorosulfonic acid

Product 1

HCID 53438971HCID 53438971, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of chlorzoxazone (10 g, 58.9 mmol) and CH2Cl2 (˜500 cm3) was added chlorosulphonic acid (4.3 cm3, 64.8 mmol) at room temperature. The reaction was left at room temperature for a week whereupon all the solvent had evaporated leaving a white solid. NMR showed a 1:2 mixture of product and starting material respectively. This crude was extracted with H2O (3×15 cm3), then the aqueous was concentrated in vacuo to a sticky solid which was washed with CH2Cl2 (4×40 cm3) to yield 5-Chloro-2-oxo-2,3-dihydro-benzooxazole-6-sulfonic acid as a fine white solid; δH (300 MHz; D6 DMSO) 7.10 (1H, s, Ar—H), 7.68 (1H, s, Ar—H) and 11.80 (1H, s, N—H); LCMS retention time ˜0.47 min, m/z (FIANEG) 247.9 [Cl35 (M−H)−, 100%] and 249.9 [Cl37 (M−H)−, 33%].

Workup

  1. waitThe reaction was left at room temperature for a week whereupon all the solvent
  2. customhad evaporated
  3. customleaving a white solid
  4. additiona 1:2 mixture of product
  5. extractionThis crude was extracted with H2O (3×15 cm3)
  6. concentrationthe aqueous was concentrated in vacuo to a sticky solid which
  7. washwas washed with CH2Cl2 (4×40 cm3)

Sources & evidence

ORD record
ord-b029aed7c94f4a9fa3b005f326be9fa2
Source dataset
uspto-grants-2006_12
Patent number
US07148236B2

Reaction notes

Loading…