Thiophenol → 4-(phenylthio)phthalazin-1(2H)-one

HRID 535506Notes

Reaction equation

HRID 535506 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.[C:13]1([SH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[C:13]1([S:19][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:12])[NH:4][N:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 27751424-chlorophthalazin-1(2H)-one

Product 1

HCID 709760554-(phenylthio)phthalazin-1(2H)-oneYield 83.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chlorophthalazin-1(2H)-one (2.1 g, 12 mmol), thiophenol (2.6 g, 23 mmol), and K2CO3 (2.4 g, 17 mmol) in DMF (40 mL) was microwaved at 125° C. for 30 minutes, diluted with EtOAc, washed with water and brine, dried (Na2SO4), filtered, concentrated, and triturated with Et2O to give the title compound (2.5 g, 10 mmol): 1H NMR (400 MHz, DMSO-d6) δ 12.88 (s, 1H), 8.28 (dd, J=7.8, 1.1, 1H), 8.06-7.99 (m, 1H), 7.98-7.92 (m, 1H), 7.92-7.85 (m, 1H), 7.44 (d, J=1.2, 2H), 7.38 (s, 3H).

Workup

  1. customwas microwaved at 125° C. for 30 minutes
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customtriturated with Et2O

Sources & evidence

ORD record
ord-6021237b62634d50a063c75fd813af68
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

Loading…