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

HRID 442730
Notes
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Reaction equation

HRID 442730 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)/[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:30])C=1.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)/[C:5](/[C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][N+:13]=1[O-:30])=[N:6]/[O:7][C:8]([CH3:11])([CH3:9])[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 135490885(E)-2-(3-bromo-alpha-t-butoxyiminobenzyl)-3-hydroxypyridine

Product 1

HCID 1364347432-[(Z)-C-(3-bromophenyl)-N-[(2-methylpropan-2-yl)oxy]carbonimidoyl]-1-oxidopyridin-1-ium-3-olYield 80%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A mixture of (Z)-2-(3-bromo-α-t-butoxyiminobenzyl)-3-hydroxypyridine (0.49 g), 70% m-chloroperbenzoic acid (0.70 g) and tetrahydrofuran (30 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 extracted 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-butoxyiminobenzyl)-3-hydroxypyridine 1-oxide (0.41 g) (compound 3). In substantially the same manner as above, compounds 4, 7, 8, 11, 12 and 15 were produced.

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. extractionextracted 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-78d0cdbe93ec4f1d9b058afdc5fef559
Source dataset
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05891895

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes