Potassium Hydroxide → HCID 89444645, compound

HRID 1522779Notes

Reaction equation

HRID 1522779 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([SH:31])([C:27]([F:30])([F:29])[F:28])[CH2:10][C:11]([C:13]2[CH:25]=[CH:24][C:16]([C:17]([NH:19][CH:20]3[CH2:23][S:22][CH2:21]3)=[O:18])=[C:15]([CH3:26])[CH:14]=2)=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:32]OS(O)(=O)=O.[OH-].[K+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:27]([F:30])([F:29])[F:28])[S:31][N:32]=[C:11]([C:13]3[CH:25]=[CH:24][C:16]([C:17]([NH:19][CH:20]4[CH2:23][S:22][CH2:21]4)=[O:18])=[C:15]([CH3:26])[CH:14]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 76284hydroxylamine-O-sulfonic acid2×HCID 89444270HCID 89444270, compound

Product 1

HCID 89444645HCID 89444645, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butyryl]-2-methyl-N-thietan-3-yl-benzamide (493 mg) dissolved in a minimum amount of tetrahydrofuran then was added Hydroxylamine-O-sulfonic acid (2 equiv.). Then a solution of potassium hydroxide (5.6 equiv.) in water (19 mL) was added dropwise. 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 crude mixture was then redissolved in a minimum amount of tetrahydrofuran then was added Hydroxylamine-O-sulfonic acid (2 equiv.) Then a solution of potassium hydroxide (5.6 equiv.) in water (19 mL) was added dropwise. 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-N-thietan-3-yl-benzamide (128 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. dissolutionThe crude mixture was then redissolved in a minimum amount of tetrahydrofuran
  8. stirringAfter stirring at room temperature for 30 minutes
  9. customthe mixture was quenched with a solution of hydrochloric acid (1N)
  10. extractionextracted with ethyl acetate
  11. washwashed with brine
  12. dry with materialThe collected organic phases were dried over magnesium sulfate
  13. filtrationfiltered
  14. customthe filtrate was evaporated under vacuo
  15. customThe residue was purified by chromatography on silica gel (eluent: cyclohexane/dichloromethane)

Sources & evidence

ORD record
ord-69e33f54b91f4e8c9497ee2927b9c536
Source dataset
uspto-grants-2015_07
Patent number
US09078444B2

Reaction notes

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