p-Toluenesulfonic acid monohydrate → HCID 58513608, compound

HRID 643693Notes

Reaction equation

HRID 643693 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:16][CH2:17][CH:18]2[CH2:20][CH2:19]2)=[C:6]([NH:8][C:9](=O)[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:16]([CH2:17][CH:18]3[CH2:20][CH2:19]3)[C:9]([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:8][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59253284HCID 59253284, compound

Product 1

HCID 58513608HCID 58513608, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of N-{5-bromo-2-[(cyclopropylmethyl)amino]phenyl}-3,3-dimethylbutanamide (Step C, 11.2 g, 33.0 mmol) and p-toluenesulfonic acid monohydrate (6.29 g, 33.0 mmol) in toluene (240 mL) was stirred at reflux temperature for 20 h with Dean-Stark apparatus. The mixture was cooled to 0° C. and a precipitate formed. The precipitate was collected by filtration washing with ethyl acetate. The precipitate was dissolved in ethyl acetate (200 mL) and saturated sodium hydrogencarbonate aqueous solution (100 mL). The organic layer was separated, washed with brine (20 mL), dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1 as eluent) to give the title compound (10.1 g, 95%) as a white solid.

Workup

  1. temperatureat reflux temperature for 20 h with Dean-Stark apparatus
  2. customa precipitate formed
  3. filtrationThe precipitate was collected by filtration
  4. washwashing with ethyl acetate
  5. dissolutionThe precipitate was dissolved in ethyl acetate (200 mL)
  6. customThe organic layer was separated
  7. washwashed with brine (20 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1 as eluent)

Sources & evidence

ORD record
ord-d6a0dce97d1741a19b28b3c843853106
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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