p-Toluenesulfonic acid monohydrate → HCID 58513608, compound

HRID 643709Notes

Reaction equation

HRID 643709 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), p-toluenesulfonic acid monohydrate (6.29 g, 33.0 mmol) and toluene (240 mL) was stirred at reflux temperature for 20 h with Dean-Stark apparatus. The mixture was cooled to 0° C. The resulting precipitate was collected by filtration and washing with small amount of ethyl acetate. The residue was dissolved in ethyl acetate (200 mL). The whole was extracted with saturated sodium hydrogen carbonate aqueous solution (100 mL). The organic layer was 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. filtrationThe resulting precipitate was collected by filtration
  3. washwashing with small amount of ethyl acetate
  4. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  5. extractionThe whole was extracted with saturated sodium hydrogen carbonate aqueous solution (100 mL)
  6. washThe organic layer was washed with brine (20 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1 as eluent)

Sources & evidence

ORD record
ord-56c111409a7344bd913f5c2594b562d6
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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