Triethylamine → N-(4-benzyloxy-2,2-difluorobutyl)-p-toluenesulfonamide

HRID 2072886Notes

Reaction equation

HRID 2072886 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]([F:15])([F:14])[CH2:12][NH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:21][CH3:22])CC)C.[C:23]1(C)[C:24]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:26]=C[CH:28]=1>ClCCl.CCOCC>[CH2:1]([O:8][CH2:9][CH2:10][C:11]([F:14])([F:15])[CH2:12][NH:13][S:29]([C:24]1[CH:25]=[CH:26][C:21]([CH3:22])=[CH:28][CH:23]=1)(=[O:31])=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 198606944-Benzyloxy-2,2-difluorobutylamine

Product 1

HCID 19860703N-(4-benzyloxy-2,2-difluorobutyl)-p-toluenesulfonamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-benzyloxy-2,2-difluorobutylamine (5.16 g, 20.5 mM) and triethylamine (4.4 g, 43.4 mM) in dry dichloromethane is added toluenesulfonyl chloride (4.14 g, 21.7 moles). The mixture is stirred at room temperature overnight. Additional dichloromethane is added, and the organic phase is washed with 1N HCl followed by a water wash. Drying (Na2SO4) and evaporation of the solvent yields a white solid which is dissolved in a small volume of ether. Addition of petroleum ether yields the compound, N-(4-benzyloxy-2,2-difluorobutyl)-p-toluenesulfonamide as white crystals: 7.0 g (92%).

Workup

  1. washthe organic phase is washed with 1N HCl
  2. washwash
  3. customDrying
  4. custom(Na2SO4) and evaporation of the solvent
  5. customyields a white solid which

Sources & evidence

ORD record
ord-c18af4d76dc849879951f3387af9ad07
Source dataset
uspto-grants-1990_04
Patent number
US04914240

Reaction notes

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