Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 21964009, compound

HRID 2212387Notes

Reaction equation

HRID 2212387 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=3[F:38])[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]4OCC[O:27]4)[CH:21]=3)=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=3[F:38])[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([C:20]3[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=3)[CH:26]=[O:27])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21048967HCID 21048967, compound

Product 1

HCID 21964009HCID 21964009, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of the product of Example 150 (73 mg, 0.13 mmol) in acetone (4 mL) and water (1 mL) was added pyridinium p-toluenesulfonate (33 mg, 0.13 mmol) and the mixture refluxed for 3.5 h. The acetone was evaporated and the residue diluted with water (10 mL) and extracted into ethyl acetate (2×10 mL). The combined organic layers were washed with saturated aqueous sodium bicarbonate (10 mL) and brine (20 mL), dried (MgSO4) and evaporated to leave the desired product (64 mg). MS (ES+) 539 ([MNa]+).

Workup

  1. temperaturethe mixture refluxed for 3.5 h
  2. customThe acetone was evaporated
  3. additionthe residue diluted with water (10 mL)
  4. extractionextracted into ethyl acetate (2×10 mL)
  5. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate (10 mL) and brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-26d3159ce46244f89d472b58a6f4d85c
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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