Water → HCID 12032054, compound

HRID 1896221Notes

Reaction equation

HRID 1896221 reaction equation
[OH-].[Na+].C([C:11]1[S:15][N:14]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[C:13](=[O:23])[CH:12]=1)(=O)C1C=CC=CC=1.O>C1C=CC=CC=1>[C:19]1([CH3:22])[CH:18]=[CH:17][C:16]([N:14]2[C:13](=[O:23])[CH:12]=[CH:11][S:15]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 12680455HCID 12680455, compound

Product 1

HCID 12032054HCID 12032054, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Aqueous sodium hydroxide (4 mL, 10%) was added to the solution of 5-benzoyl-2-p-tolylisothiazol-3-one 29 (203 mg, 0.678 mmol) in benzene (9 mL), and the mixture was stirred for 3 d at room temperature. The reaction mixture was added water (20 mL) and extracted with ethyl acetate. The combined organic layer was dried (MgSO4), filtered and evaporated. The residue was purified by flash silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1) and gave the compound 30 (77 mg, 59%). 1H-1-NMR (CDCl3, 300 MHz) δ 2.38 (s, 3H), 6.32 (d, J=6.6 Hz, 1H), 7.25 (d, J=8.1 Hz, 2H), 7.44 (d, J=8.1 Hz, 2H), 8.14 (d, J=6.6 Hz, 1H). HRMS: calculated for C10H10NOS (M+H)+192.0483. Found 192.0494.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1)

Sources & evidence

ORD record
ord-f3bab8755ec44f0a80b572469a4f090f
Source dataset
uspto-grants-2013_08
Patent number
US08518957B2

Reaction notes

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