p-Toluenesulfonic acid monohydrate → HCID 69422345, compound

HRID 1295842Notes

Reaction equation

HRID 1295842 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[N:18]([C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[CH2:17][CH2:16][N:6]2[C:7]=1[C:8](O)([CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10][CH3:11])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[N:4]=[C:5]2[N:18]([C:19]3[C:20]([CH3:27])=[CH:21][C:22]([CH3:26])=[CH:23][C:24]=3[CH3:25])[CH2:17][CH2:16][N:6]2[C:7]=1[C:8]([CH2:12][CH2:13][CH3:14])=[CH:9][CH2:10][CH3:11])[CH3:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21916117HCID 21916117, compound

Product 1

HCID 69422345HCID 69422345, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-[2-ethyl-7-(2,4,6-trimethyl-phenyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazol-3-yl]-heptan-4-ol (0.0444 g, 0.000120 mol) and p-toluenesulfonic acid-H2O (15 mole %) in toluene (3 mL) was heated at reflux for 1 h. Upon cooling to room temperature, the solvent was evaporated under reduced pressure, and the residue was partitioned between ether and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over anhydrous Na2SO4, and concentrated to give the desired product in quantitative yield. LC-MS indicated the presence of two regioisomers in an approximate ratio of 2:1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was partitioned between ether and saturated aqueous sodium bicarbonate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ca973a4915c643338f9201915ca3f98c
Source dataset
uspto-grants-2007_07
Patent number
US07244746B2

Reaction notes

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