Hydrochloric Acid → HCID 22316755, compound

HRID 1597521Notes

Reaction equation

HRID 1597521 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[N:15]=[C:14]([C:27]([O:29]CC)=[O:28])[CH:13]=2)=[CH:8][CH:7]=1.C1COCC1.[Na].Cl>C(O)C.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:24])=[O:25])=[CH:19][CH:18]=3)[N:15]=[C:14]([C:27]([OH:29])=[O:28])[CH:13]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 5360545SodiumHCID 22316679HCID 22316679, compound

Product 1

HCID 22316755HCID 22316755, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of Ethyl 5-[4-(2-furyl)phenyl]-1-[4-(methylsulfonyl)phenyl]-1H-pyrazole-3-carboxylate (prepared according to the procedure of Example 63, step 1) (0.1 g) in ethanol (5 mL)-THF (3 mL) was added 2N-Sodium hydroxied solution in water (1 mL) and the mixture was heated at reflux temperature for 1.5 hours. After cooling, 2N-HCl solution (2 mL) and water (20 mL) were added to the mixture. The whole was extracted with CH2Cl2 (50 mL×2), the organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The resulting solid was recrystallized with isopropanol-water to give the title compound (0.08 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 1.5 hours
  3. temperatureAfter cooling
  4. extractionThe whole was extracted with CH2Cl2 (50 mL×2)
  5. washthe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resulting solid was recrystallized with isopropanol-water

Sources & evidence

ORD record
ord-b74d2eb7fa624826bc0cef5d13b3ca65
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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