Sodium Sulfite → HCID 19735134, compound

HRID 326578Notes

Reaction equation

HRID 326578 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](C(OO)=O)[CH:3]=1.[CH3:12][C:13]1([CH3:31])[NH:18][C:17](=[O:19])[C:16]2[CH:20]=[C:21](SC3C=CC=CC=3)[CH:22]=[CH:23][C:15]=2[O:14]1.[S:32]([O-:35])([O-])=[O:33].[Na+].[Na+]>ClCCl>[CH3:12][C:13]1([CH3:31])[NH:18][C:17](=[O:19])[C:16]2[CH:20]=[C:21]([S:32]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)(=[O:35])=[O:33])[CH:22]=[CH:23][C:15]=2[O:14]1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 19735140HCID 19735140, compound

Product 1

HCID 19735134HCID 19735134, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (70% purity, 4.64 g) was added with ice-cooling to a solution of 2,2-dimethyl-6-phenylthio-3,4-dihydro-2H-1,3-benzoxazin-4-one (2.24 g) in dichloromethane (50 ml) and the mixture was stirred for 30 minutes. The reaction mixture was poured into an aqueous sodium sulfite solution and the mixture was extracted by addition of ethyl acetate. The organic layer was successively washed with an aqueous sodium carbonate solution and saturated saline solution, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was washed with isopropyl ether to obtain 2,2-dimethyl-6-phenylsulfonyl-3,4-dihydro-2H-1,3-benzoxazin-4-one (2.50 g) (Compound A-13). The physical properties are shown in Table 1.

Workup

  1. extractionthe mixture was extracted by addition of ethyl acetate
  2. washThe organic layer was successively washed with an aqueous sodium carbonate solution and saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. washThe residue was washed with isopropyl ether

Sources & evidence

ORD record
ord-39b3fd8352d24bc79e286f9105fc44b5
Source dataset
uspto-grants-1993_12
Patent number
US05270308

Reaction notes

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