2,4-Difluorobenzenesulfonyl Chloride → N-(2-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2,4-difluoro-N-methylbenzenesulfonamide

HRID 548730Notes

Reaction equation

HRID 548730 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[Si:13]([O:20][CH2:21][CH2:22][NH:23][CH3:24])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>C(Cl)Cl.[OH-].[Na+]>[CH3:19][C:16]([Si:13]([CH3:14])([CH3:15])[O:20][CH2:21][CH2:22][N:23]([CH3:24])[S:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])(=[O:11])=[O:10])([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 27342732,4-Difluorobenzenesulfonyl ChlorideHCID 16203640N-(2-(tert-Butyldimethylsilyloxy)ethyl)methylamine

Product 1

HCID 57663205N-(2-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2,4-difluoro-N-methylbenzenesulfonamideYield 40.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

2,4-Difluorobenzenesulfonyl chloride (1 g, 4.70 mmol) in DCM (2 mL) was added slowly to a solution of (2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)methylamine (980 mg, 5.17 mmol) in DCM (65 mL) and 10% sodium hydroxide solution (65 mL) at 0° C. The reaction was allowed to warm to RT and stirred for 20 hours. The DCM layer was separated and the aqueous re-extracted into DCM (2×50 mL). The combined organics were washed with brine (80 mL), dried (MgSO4), and reduced in vacuo to give the desired compound as a colourless oil (0.7 g). 1H NMR δ (CDCl3): 0.00 (s, 6H), 0.83 (s, 9H), 2.91 (s, 3H), 3.24 (t, 2H), 3.73 (t, 2H), 6.87-6.96 (m, 2H), 7.82-7.88 (m, 1H)

Workup

  1. customThe DCM layer was separated
  2. extractionthe aqueous re-extracted into DCM (2×50 mL)
  3. washThe combined organics were washed with brine (80 mL)
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-0e5d01cc5a474f6c8d717c6ecfa1abfb
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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