Sodium Sulfite → 2-[(Z)-C-(3-bromo-4-fluorophenyl)-N-[(2-methylpropan-2-yl)oxy]carbonimidoyl]-1-oxidopyridin-1-ium-3-ol

HRID 442732Notes

Reaction equation

HRID 442732 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[F:22])/[C:5](/[C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][N:13]=1)=[N:6]/[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].ClC1C=CC=C(C(OO)=[O:31])C=1.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[F:22])/[C:5](/[C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][N+:13]=1[O-:31])=[N:6]/[O:7][C:8]([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 135494341(E)-2-(3-bromo-alpha-t-butoxyimino-4-fluorobenzyl)-3-hydroxypyridine

Product 1

HCID 1364347372-[(Z)-C-(3-bromo-4-fluorophenyl)-N-[(2-methylpropan-2-yl)oxy]carbonimidoyl]-1-oxidopyridin-1-ium-3-olYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (Z)-2-(3-bromo-α-t-butoxyimino-4-fluorobenzyl)-3-hydroxypyridine (0.55 g), 70% m-chloro perbenzoic acid (0.74 g) and tetrahydrofuran (10 mL) was stirred overnight at room temperature. To the reaction mixture was added an aqueous solution of sodium sulfite. The reaction mixture was stirred for 30 minutes, and subjecting to extraction with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, successively, and dried (sodium sulfate) and then concentrated. The concentrate was crystallized from isopropyl ether, and recrystallized from ethanol-water to afford (Z)-2-(3-bromo-α-t-butoxyimino-4-fluorobenzyl)-3-hydroxypyridine 1-oxide (0.46 g) (compound 25).

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. extractionsubjecting to extraction with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous saline solution, successively, and dried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was crystallized from isopropyl ether
  7. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-2736ca13e9584df29310e581d3141833
Source dataset
uspto-grants-1999_04
Patent number
US05891895

Reaction notes

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