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Potassium Hydroxide → tert-butyl 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoate

HRID 1522775
Notes
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Reaction equation

HRID 1522775 reaction equation
[C:1]([O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=O)[CH2:14][C:15]([C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)([SH:20])[C:16]([F:19])([F:18])[F:17])=[CH:9][C:8]=1[CH3:30])([CH3:4])([CH3:3])[CH3:2].[NH2:32]OS(O)(=O)=O.[OH-].[K+]>O1CCCC1>[C:1]([O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:14][C:15]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([C:16]([F:19])([F:18])[F:17])[S:20][N:32]=2)=[CH:9][C:8]=1[CH3:30])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 894445754-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butyryl]-2-methyl-benzoic acid tert-butyl ester

Product 1

HCID 89444266tert-butyl 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 4-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butyryl]-2-methyl-benzoic acid tert-butyl ester (1.875 g) in tetrahydrofuran (6 mL) was added a solution of Hydroxylamine-O-sulfonic acid (2 equiv.) in a solution of potassium hydroxide (1.2 g in 75 mL of water). After stirring at room temperature for 30 minutes, the mixture was quenched with a solution of hydrochloric acid (1N), extracted with ethyl acetate and washed with brine. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/dichloromethane) to give 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isothiazol-3-yl]-2-methyl-benzoic acid tert-butyl ester (881 mg)

Workup

  1. customthe mixture was quenched with a solution of hydrochloric acid (1N)
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe collected organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated under vacuo
  7. customThe residue was purified by chromatography on silica gel (eluent: cyclohexane/dichloromethane)

Sources & evidence

ORD record
ord-981ffeeb3fbc4159ac357b8b69c0f8c9
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09078444B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes