Potassium Carbonate → 4-(tert-butylthio)phthalazin-1(2H)-one

HRID 535614Notes

Reaction equation

HRID 535614 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][N:3]=1.[CH3:13][C:14]([S-:17])([CH3:16])[CH3:15].[Na+].C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.FC(F)(F)S(O[Sc](OS(C(F)(F)F)(=O)=O)OS(C(F)(F)F)(=O)=O)(=O)=O>[C:14]([S:17][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][N:3]=1)([CH3:16])([CH3:15])[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27751424-chlorophthalazin-1(2H)-oneHCID 5147913Sodium 2-methyl-2-propanethiolate

Product 1

HCID 709760764-(tert-butylthio)phthalazin-1(2H)-oneYield 20%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-chlorophthalazin-1(2H)-one (200 mg, 1.11 mmol), sodium 2-methylpropane-2-thiolate (248 mg, 2.22 mmol), tris(trifluoromethylsulfonyloxy)scandium (54.5 mg, 0.11 mmol) and K2CO3 (308 mg, 2.22 mmol) was heated at 160° C. under microwave condition for 30 minutes. The mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3, dried (Na2SO4), filtered, and chromatographed (0-30% EtOAc/DCM) to give 52 mg (20%) of the title compound as a white solid: MS (DCI) 235 (M+H).

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customchromatographed (0-30% EtOAc/DCM)

Sources & evidence

ORD record
ord-432221f68edb4850bf7a66283e5b5b6f
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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