Sodium Sulfite → HCID 136463710, compound

HRID 862105Notes

Reaction equation

HRID 862105 reaction equation
[C:1]([O:5]/[N:6]=[C:7](\[C:16]1[C:21]([C:22]#[N:23])=[CH:20][CH:19]=[CH:18][N:17]=1)/[C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:32])C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5]/[N:6]=[C:7](\[C:16]1[C:21]([C:22]#[N:23])=[CH:20][CH:19]=[CH:18][N+:17]=1[O-:32])/[C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=1[OH:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 136463748HCID 136463748, compound

Product 1

HCID 136463710HCID 136463710, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of (Z)-2-(5-bromo-2-hydroxybenzoyl)-3-cyanopyridine O-t-butyloxime (350 mg) and 50% m-chloroperbenzoic acid (710 mg) in chloroform (5 ml) was stirred for 6 hours at 50° C. The reaction mixture was cooled by aeration, which was poured into an aqueous solution of sodium sulfite. The mixture was stirred and subjected to extraction with chloroform. The extract solution was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, dried (anhydrous sodium sulfate), and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane) to give (Z)-2-(5-bromo-2-hydroxybenzoyl)-3-cyanopyridine N-oxide O-t-butyloxime (120 mg) (Compound 145).

Workup

  1. temperatureThe reaction mixture was cooled by aeration, which
  2. extractionsubjected to extraction with chloroform
  3. washThe extract solution was washed successively with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materiala saturated aqueous saline solution, dried (anhydrous sodium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-28db5c9a78d64ef48f1d8ac7d07183e6
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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