Methanol → HCID 22609710, compound

HRID 2306698Notes

Reaction equation

HRID 2306698 reaction equation
CS[CH2:3][CH2:4][NH:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8].O[O:13][S:14]([O-:16])=O.[K+].OS([O-])(=O)=O.[K+].[CH3:24]O>O>[CH3:24][S:14]([CH2:3][CH2:4][NH:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])(=[O:16])=[O:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 516920Potassium bisulfateHCID 22609837HCID 22609837, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22609710HCID 22609710, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-(2-methylthioethyl) trifluoroacetamide (19.0 g, 109.7 mmol) in methanol (200 ml) was cooled to 0° C. using an ice bath. A suspension of Oxone™ (2KHSO5.KHSO4.K2SO4) (74.19 g, 120.67 mmol) in water (100 ml) was added portionwise over 10 minutes, and the reaction was stirred at room temperature for 24 hours. The methanol was removed in vacuo, water (600 ml) was added and the mixture was extracted with dichloromethane (3×300 ml). The combined extracts were dried (MgSO4), and concentrated in vacuo to give the title compound as a white solid (12.42 g, 56.7 mmol, 52%); δH CDCl3 7.33 (1H, br s), 3.93 (2H, q), 3.31 (2H, t), 3.02 (3H, s).

Workup

  1. additionwas added portionwise over 10 minutes
  2. customThe methanol was removed in vacuo, water (600 ml)
  3. additionwas added
  4. extractionthe mixture was extracted with dichloromethane (3×300 ml)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-83e4026e94c848ee9d6bda5bb01c31b9
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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