Hydrochloric Acid → 5-Isothiazolecarboxylic acid, 3-(3-(trifluoromethyl)phenyl)-

HRID 67649Notes

Reaction equation

HRID 67649 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[CH:13]=[C:12]([C:14]([O:16]C)=[O:15])[S:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.[OH-].[K+].Cl.FC(F)(F)C1C=C(C2C=C(C([O-])=O)SN=2)C=CC=1>>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[S:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13073224Methyl 3-(3-trifluoromethylphenyl)-5-isothiazolecarboxylateHCID 867385453-(3-Trifluoromethylphenyl)-5-isothiazolecarboxylate

Product 1

HCID 30679245-Isothiazolecarboxylic acid, 3-(3-(trifluoromethyl)phenyl)-Yield 85%

Procedure

A solution of 1.6 g. of methyl 3-(3-trifluoromethylphenyl)-5-isothiazolecarboxylate in 30 ml. of 95% alcohol containing 1.0 g. of potassium hydroxide was heated at reflux for one hour. The reaction mixture then was added to 50 g. of ice, and the aqueous solution was acidified by the addition of 12 N aqueous hydrochloric acid. The product which precipitated was collected by filtration and crystallized from toluene and hexane to provide 1.3 g. of 3-(3-trifluoromethylphenyl)-5-isothiazolecarboxylate acid. Yield 85%. M.P. 162.5°-164° C.

Workup

  1. temperatureat reflux for one hour
  2. additionThe reaction mixture then was added to 50 g
  3. customThe product which precipitated
  4. filtrationwas collected by filtration
  5. customcrystallized from toluene and hexane
  6. customto provide 1.3 g

Sources & evidence

ORD record
ord-7997b32bf61d49c8a04a6b7b00f35295
Source dataset
uspto-grants-1982_08
Patent number
US04346094

Reaction notes

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