Sodium Sulfite → HCID 178474150, compound

HRID 1772910Notes

Reaction equation

HRID 1772910 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:22])[CH3:21])=[N:17][CH:18]=1.[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:20]([NH:19][C:16]1[CH:15]=[CH:14][C:13]([CH3:12])=[CH:18][N+:17]=1[O-:9])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 818995N-(5-Methyl-2-pyridyl)acetamide

Product 1

HCID 178474150HCID 178474150, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-CPBA (75% in H2O, 89.6 g, 390 mmol) was added portion wise to a stirred solution of N-(5-methylpyridin-2-yl)acetamide (45.0 g, 300 mmol) in DCM (2.7 L) at rt, and the mixture stirred at rt for 4 h. 5% aqueous Na2SO3 (200 mL) was added slowly, the phases were separated and the organic layer washed with saturated NaHCO3, brine (100 mL), dried (MgSO4) and filtered. After concentration in vacuo purification by gradient column chromatography eluting with 2-5% MeOH in DCM yielded the title compound (37.5 g, 243 mmol) as a pale yellow solid.

Workup

  1. customthe phases were separated
  2. washthe organic layer washed with saturated NaHCO3, brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationAfter concentration
  6. customin vacuo purification by gradient column chromatography
  7. washeluting with 2-5% MeOH in DCM

Sources & evidence

ORD record
ord-2582016e5df74018ba92924460f5d424
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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