Sodium Sulfite → HCID 9999062, compound

HRID 326595Notes

Reaction equation

HRID 326595 reaction equation
[Br:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1.ClC1C=CC=C(C(OO)=[O:29])C=1.S([O-])([O-])=O.[Na+].[Na+]>ClCCl.O>[Br:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N+:14]=3[O-:29])[C:6]=2[CH:19]=1

Participants

6

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 10712934HCID 10712934, compound

Product 1

HCID 9999062HCID 9999062, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound 88(10.0 g) in dichloromethane (130 ml) was added 70% m-chloroperbenzoic acid (20.0 g) at 0° C. and the mixture was stirred at 2° to 4° C. for 5 hours. A solution of sodium sulfite (32 g) in water (130 ml) was added slowly and stirred for 1 hour with ice-cooling. The organic layer was separated, washed successively with 5% aqueous sodium carbonate solution and saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by chromatography on silica gel and crystallized from diethyl ether to obtain 2-(6-bromo-7-chloro-2,2-dimethyl-2H-1,3-benzoxazin-4-yl)pyridine 1-oxide (2.7 g) (Compound 89).

Workup

  1. stirringstirred for 1 hour with ice-
  2. temperaturecooling
  3. customThe organic layer was separated
  4. washwashed successively with 5% aqueous sodium carbonate solution and saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by chromatography on silica gel
  8. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-5759c0b1ac0e490d8b19ff1c0d204141
Source dataset
uspto-grants-1993_12
Patent number
US05270308

Reaction notes

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