Sodium hydride → N-benzyl-N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide

HRID 1665003Notes

Reaction equation

HRID 1665003 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH2:7][NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+]>CN(C)C(=O)C>[CH2:18]([N:8]([CH2:7][C:5]1[S:6][C:2]([Br:1])=[CH:3][CH:4]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:19])([F:21])[F:20])(=[O:11])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:12]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 35408897N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide

Product 1

HCID 67439229N-benzyl-N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamideYield 152.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred solution of N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide (0.594 g) in N,N-dimethylacetamide (4 mL) was added NaH (dispersion, ca 55% in oil, 0.039 g) at 0° C. After stirring for 5 min, the ice bath was removed and the mixture was stirred for 50 min. Benzyl bromide (0.28 g) was added and the mixture was stirred overnight at r.t. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The product was purified by chromatography (SiO2, cyclohexane to cyclohexane/ethyl acetate 2:1) to give N-benzyl-N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide (0.555 g) as a colorless solid. MS: 490 ([M+H]+)

Workup

  1. customthe ice bath was removed
  2. stirringthe mixture was stirred for 50 min
  3. additionBenzyl bromide (0.28 g) was added
  4. stirringthe mixture was stirred overnight at r.t
  5. additionWater was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe product was purified by chromatography (SiO2, cyclohexane to cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-328568dcdb9d47c6862a7fad7772ac6e
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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