Sodium hydride → HCID 86658341, compound

HRID 2198037Notes

Reaction equation

HRID 2198037 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([NH:13][S:14]([CH2:17][CH2:18][CH2:19]Cl)(=[O:16])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([N:13]2[CH2:19][CH2:18][CH2:17][S:14]2(=[O:16])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86658340HCID 86658340, compound

Product 1

HCID 86658341HCID 86658341, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[3,5-bis(trifluoromethyl)phenyl]-3-chloropropanesulfonamide (7.10) obtained in Reference Example 37 in N,N-dimethylformamide (100 mL) was added sodium hydride (60% in oil, 0.84 g), and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added saturated ammonium chloride and the solution was partitioned between ethyl acetate and water. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 90:10-40:60) to give the title compound (2.44 g, yield 38%) as a pale-brown solid.

Workup

  1. customthe solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 90:10-40:60)

Sources & evidence

ORD record
ord-a32995d082f34b7bb8f680373d85a495
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

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