Hydrochloric Acid → 3-Phenyl-4-(trifluoromethyl)isothiazole-5-carboxylic acid

HRID 1948544Notes

Reaction equation

HRID 1948544 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([O:18]C)=[O:17])[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-].Cl>C1COCC1>[C:1]1([C:7]2[C:11]([C:12]([F:13])([F:14])[F:15])=[C:10]([C:16]([OH:18])=[O:17])[S:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58374139Methyl 3-phenyl-4-(trifluoromethyl)isothiazole-5-carboxylate

Product 1

HCID 583740793-Phenyl-4-(trifluoromethyl)isothiazole-5-carboxylic acidYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-phenyl-4-(trifluoromethyl)isothiazole-5-carboxylate (50 mg, 0.174 mmol) in THF (0.5 mL) was added a 1M LiOH solution (0.2mL). The resulting mixture was stirred at room temperature overnight. The pH of the reaction mixture was made acidic using 1N HCl and the solid that separates out was collected by filtration and dried in vacuo to yield 3-phenyl-4-(trifluoromethyl)isothiazole-5-carboxylic acid (42 mg, 0.154 mmol, 88% yield) as a pale yellow solid. LC/MS M+1=274.

Workup

  1. filtrationthe solid that separates out was collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-a9a35665ef9340fe94576832bd39921f
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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