Sodium Pyrosulfite → HCID 18630134, compound

HRID 725517Notes

Reaction equation

HRID 725517 reaction equation
[CH2:1]([NH:3][C:4](=[O:17])[C:5]1[C:10]([S:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][CH:8]=[CH:7][C:6]=1[F:16])[CH3:2].[OH:18]OS([O-])=O.[K+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CO.O>[CH3:14][C:12]([S:11]([C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([F:16])[C:5]=1[C:4]([NH:3][CH2:1][CH3:2])=[O:17])=[O:18])([CH3:13])[CH3:15]

Participants

6

Reactant 3

HCID 656671Sodium PyrosulfiteHCID 18630040HCID 18630040, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18630134HCID 18630134, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A 0° C. solution of N-ethyl-2-fluoro-6-(1,1-dimethylethylthio)benzamide (3.45 g, 13.51 mmol) in methanol (100 mL) was combined with a 0° C. solution of OXONE® (8.31 g, 13.51 mmol) in water (100 mL). This mixture was stirred for 2 min, then was poured into 25% aq sodium metabisulfite (100 mL) and extracted with ether (3×100 mL). The combined organics were washed with brine followed with water, then was dried (MgSO4), concentrated, and recrystallized from ethyl acetate-hexanes to afford 2.2 g of the title compound as a white solid, a 60% yield. m.p. 114°-116° C.

Workup

  1. customwas combined with a 0° C.
  2. extractionextracted with ether (3×100 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated
  6. customrecrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-98964901b5114237b2bbf3c7a5184da1
Source dataset
uspto-grants-1998_01
Patent number
US05705513

Reaction notes

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