Hydrochloric Acid → Cimicoxib

HRID 898755Notes

Reaction equation

HRID 898755 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([F:28])[CH:21]=3)=[C:18]([Cl:29])[N:17]=[CH:16]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C.Cl.[OH-].[Na+]>O>[Cl:29][C:18]1[N:17]=[CH:16][N:15]([C:12]2[CH:11]=[CH:10][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:14][CH:13]=2)[C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([F:28])[CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 102748154-(4-Chloro-5-(3-fluoro-4-methoxyphenyl)-1H-imidazol-1-yl)-N-(1,1-dimethylethyl)benzenesulfonamide

Product 1

HCID 213053CimicoxibYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-tert-butyl-4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazol-1-yl]benzenesulfonamide (37.0 g, 85 mmol, obtained in example 4), concentrated HCl (200 mL) and H2O (200 mL) is heated at reflux for 3 h. The mixture is allowed to cool and is brought to pH 6 with 6N NaOH. A white precipitate appears, which is collected by filtration and washed with plenty of H2O and then with CHCl3. 31 g of the title compound of the example is obtained (yield: 97%), which are recrystallized from acetonitrile.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 h
  3. temperatureto cool
  4. filtrationwhich is collected by filtration
  5. washwashed with plenty of H2O
  6. customare recrystallized from acetonitrile

Sources & evidence

ORD record
ord-57e84273db7e438f98c773ad3a770a0c
Source dataset
uspto-grants-2008_04
Patent number
US07351836B2

Reaction notes

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