Water → HCID 68525955, compound

HRID 2247739Notes

Reaction equation

HRID 2247739 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:16]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:23][CH:22]=3)[O:18][N:17]=2)[S:6][C:7]=1[CH2:8][O:9]C1CCCCO1)[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>C(O)C>[CH2:1]([C:3]1[CH:4]=[C:5]([C:16]2[N:20]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([O:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[CH:25][CH:26]=3)[O:18][N:17]=2)[S:6][C:7]=1[CH2:8][OH:9])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 68521959HCID 68521959, compound

Product 1

HCID 68525955HCID 68525955, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-{4-ethyl-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2-thienyl}-5-(4-phenoxyphenyl)-1,2,4-oxadiazole (0.25 g, 0.54 mmol) that was obtained in Example 22 (22e) in ethanol (5 ml) was added pyridinium p-toluenesulfonate (0.014 g, 0.54 mmol) with stirring, and the resulting mixture was stirred at 60° C. for 4 hours. After stirring, the reaction mixture was poured into water (20 ml) to quench the reaction and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo to afford the title compound (0.19 g) in a yield of 92% as a crystalline white solid.

Workup

  1. stirringthe resulting mixture was stirred at 60° C. for 4 hours
  2. stirringAfter stirring
  3. customto quench
  4. customthe reaction
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationAfter filtration
  9. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-9a6d744897264f959c8edb0c0f0f5a15
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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