Hydrochloric Acid → 2-(2,6-Difluorobenzamido)-5-(3-(trifluoromethyl)phenyl)thiazole-4-carboxylic acid

HRID 1255128Notes

Reaction equation

HRID 1255128 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[C:10]([C:12]([O:14]C)=[O:13])[N:11]=1)=[O:5].[OH-].[Na+].Cl>CO>[F:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:2]([F:1])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=2)=[C:10]([C:12]([OH:14])=[O:13])[N:11]=1)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24765114Methyl 2-(2,6-difluorobenzamido)-5-(3-(trifluoromethyl)phenyl)thiazole-4-carboxylate

Product 1

HCID 590044862-(2,6-Difluorobenzamido)-5-(3-(trifluoromethyl)phenyl)thiazole-4-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a solution of Compound 35 (884 mg, 2 mmol) in 20 mL of MeOH was added NaOH (400 mg, 10 mmol). The solution was heated to reflux for 1 hour and cooled down to room temperature. The reaction was neutralized with 2N HCl and extracted with Et2O. The combined extracts were washed with water, dried (Na2SO4), filtered and concentrated. Recrystallization from Et2O gave Compound 66 (810 mg, 95%) as a white solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 hour
  3. extractionextracted with Et2O
  4. washThe combined extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customRecrystallization from Et2O

Sources & evidence

ORD record
ord-fa1466a6875843c2b2096ea3a47d692d
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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