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

HRID 2309598Notes

Reaction equation

HRID 2309598 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 folllowed 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-77aae6a0dbbe425cb0b2cfa2b1230cee
Source dataset
uspto-grants-1987_09
Patent number
US04695654

Reaction notes

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