Water → HCID 9816197, compound

HRID 1934352Notes

Reaction equation

HRID 1934352 reaction equation
[OH:1][CH:2]([CH3:17])[C:3]([NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15])([CH3:5])[CH3:4].C(N(CC)CC)C.O>CS(C)=O>[O:1]=[C:2]([CH3:17])[C:3]([NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 9816246HCID 9816246, compound

Product 1

HCID 9816197HCID 9816197, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N-(2-hydroxy-1,1-dimethylpropyl)-2,4-difluorobenzamide obtained in Example 33 (0.30 g, 1.2 mmol) and triethylamine (0.37 g, 3.7 mmol) in DMSO (3 ml) was added pyridine sulfur trioxide complex (0.59 g, 3.7 mmol) portionwise and stirred at room temperature for 3 hours. The reaction mixture was added to a mixture of ice and water and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, saturated aqueous NaHCO3 and brine, successively dried over Na2SO4 and concentrated under a reduced pressure. The residue was crystallized from hexane/ethyl acetate to give the title compound (0.24 g; 81%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 1N hydrochloric acid, saturated aqueous NaHCO3 and brine
  3. dry with materialsuccessively dried over Na2SO4
  4. concentrationconcentrated under a reduced pressure
  5. customThe residue was crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-36d351bcf99c45b5959398c94bacbd42
Source dataset
uspto-grants-2002_05
Patent number
US06384033B1

Reaction notes

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