Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 58847342, compound

HRID 1272333Notes

Reaction equation

HRID 1272333 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:18]1CCO[CH:19]1[C:23]1[C:31]2[O:30][C:29]([CH3:33])([CH3:32])[CH:28]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)[C:27]=2[C:26]([CH3:41])=[C:25]([N:42]2[CH2:47][CH2:46][N:45]([C:48]3[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=3)[CH2:44][CH2:43]2)[C:24]=1[CH3:56]>CC(C)=O.O>[CH3:55][O:54][C:51]1[CH:50]=[CH:49][C:48]([N:45]2[CH2:46][CH2:47][N:42]([C:25]3[C:24]([CH3:56])=[C:23]([CH:19]=[O:18])[C:31]4[O:30][C:29]([CH3:33])([CH3:32])[CH:28]([C:34]5[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=5)[C:27]=4[C:26]=3[CH3:41])[CH2:43][CH2:44]2)=[CH:53][CH:52]=1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10143110HCID 10143110, compound

Product 1

HCID 58847342HCID 58847342, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Pyridinium p-toluenesulfonate (20 mg, 80 mmol) was added to a solution of 1-(7-(1,3-dioxolan-2-yl)-2,2,4,6-tetramethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine (1.41 g, 2.67 mmol) obtained in Example 93 in acetone (15 ml) and water (1 ml) and the mixture was refluxed for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from hexane-ethyl acetate to obtain 1.04 g (yield 81%) of the title compound. mp. 175–177° C.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-0eaadd17485245859bef5acdd61f210d
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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