Potassium Carbonate → HCID 22482367, compound

HRID 2181886Notes

Reaction equation

HRID 2181886 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH:13]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2F)[CH3:14])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:28][C:25]1[CH:26]=[CH:27][C:22]2[C:16]3[C:15]([CH:13]([CH3:14])[N:12]([S:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)(=[O:10])=[O:11])[C:23]=2[CH:24]=1)=[CH:20][C:19]([F:21])=[CH:18][CH:17]=3

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22482359HCID 22482359, compound

Product 1

HCID 22482367HCID 22482367, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred suspension of 4-methoxy-N-[1-(2′,4,4′-trifluoro-1,1′-biphenyl-2-yl)ethyl]benzenesulfonamide (0.74 g, 1.74 mmol) and potassium carbonate (0.48 g, 3.50 mmol) in N,N-dimethylformamide (5 mL) was heated for twelve hours at 100° C. The reaction mixture was cooled and poured into distilled water. After stirring overnight at room temperature, a precipitate was filtered and dried under high vacuum. The precipitate was purified by preparative liquid chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g), eluting with a mixture of 15% methyl tert-butyl ether in hexane at a flow rate of 50 mL/min to afford, after evaporation of the solvent, a colorless solid. Crystallization from diethyl ether-hexane yielded the title compound (0.67 g, 1.65 mmol, 95%) as a homogeneous, colorless, crystalline solid, m.p. 141-143° C.;

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionpoured
  3. distillationinto distilled water
  4. filtrationa precipitate was filtered
  5. customdried under high vacuum
  6. customThe precipitate was purified by preparative liquid chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g)
  7. washeluting with a mixture of 15% methyl tert-butyl ether in hexane at a flow rate of 50 mL/min
  8. customto afford
  9. customafter evaporation of the solvent
  10. customCrystallization from diethyl ether-hexane

Sources & evidence

ORD record
ord-4ac70551d42c4ce4aaf4747d582c5f4d
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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