Potassium Hydroxide → HCID 89444536, compound

HRID 1522773Notes

Reaction equation

HRID 1522773 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)([SH:15])[C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[CH3:25].[OH-].[K+].[NH2:28]OS(O)(=O)=O>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][C:10]([C:16]3[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=3)([C:11]([F:14])([F:13])[F:12])[S:15][N:28]=2)=[CH:4][C:3]=1[CH3:25]

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 76284hydroxylamine-O-sulfonic acidHCID 89444584HCID 89444584, compound

Product 1

HCID 89444536HCID 89444536, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butan-1-one (382 mg) in a solution of potassium hydroxide (162 mg in 8 mL of water) was added a solution of Hydroxylamine-O-sulfonic acid (2 equiv.) in a solution of potassium hydroxide (243 mg in 16 mL of water). After stirring at room temperature for 30 minutes, the mixture was diluted 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 3-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isothiazole (184 mg).

Workup

  1. washwashed with brine
  2. dry with materialThe collected organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe filtrate was evaporated under vacuo
  5. customThe residue was purified by chromatography on silica gel (eluent: cyclohexane/dichloromethane)

Sources & evidence

ORD record
ord-846150ab14334d62af8ab7bb32185e14
Source dataset
uspto-grants-2015_07
Patent number
US09078444B2

Reaction notes

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