Sodium Pyrosulfite → HCID 18630177, compound

HRID 356390Notes

Reaction equation

HRID 356390 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5](=[O:18])[C:6]1[C:11]([S:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:10][CH:9]=[CH:8][C:7]=1[F:17].[OH:19]OS([O-])=O.[K+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CO.O>[Cl:1][CH2:2][CH2:3][NH:4][C:5](=[O:18])[C:6]1[C:7]([F:17])=[CH:8][CH:9]=[CH:10][C:11]=1[S:12]([C:13]([CH3:14])([CH3:15])[CH3:16])=[O:19]

Participants

6

Reactant 3

HCID 656671Sodium PyrosulfiteHCID 18630187HCID 18630187, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18630177HCID 18630177, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A 0° C. solution of N-(2-chloroethyl)-2-fluoro-6-(1,1-dimethylethylthio)benzamide (2.0 g, 7.0 mmol) in methanol (50 mL) was combined with a 0° C. solution of OXONE® (4.24 g, 7.0 mmol) in water (50 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 were dried (MgSO4), concentrated, and purified by HPLC with 7:3 ethyl acetate/hexanes to afford 2.1 g of the title compound as a white solid, a 98% yield. m.p. 80°-90° 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 materialwere dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by HPLC with 7:3 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7f2919cf524e47febc3a418579aad263
Source dataset
uspto-grants-1998_11
Patent number
US05834447

Reaction notes

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