Ethylene Glycol → HCID 70975942, compound

HRID 535608Notes

Reaction equation

HRID 535608 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]1[CH:19]=[CH:18][C:17]([S:20]([O-])=O)=[CH:16][CH:15]=1.[Na+].C(O)CO>CN1CCCC1=O.CCOC(C)=O>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][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:16][CH:15]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 2723791Sodium p-toluenesulfinateHCID 27751424-chlorophthalazin-1(2H)-one

Product 1

HCID 70975942HCID 70975942, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-chlorophthalazin-1(2H)-one (0.233 g, 1.29 mmol) and sodium 4-methylbenzenesulfinate (0.460 g, 2.58 mmol) in ethane-1,2-diol (0.29 mL, 5.19 mmol) and methyl-2-pyrrolidinone (2.6 mL) was microwaved at 230° C. for 30 minutes, diluted with EtOAc, washed with water and brine, dried (Na2SO4), filtered, and chromatographed (15% EtOAc/DCM) to give 0.260 g of impure title compound as a white solid: MS (APCI+) M/Z 269 (M+H)+.

Workup

  1. customwas microwaved at 230° C. for 30 minutes
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customchromatographed (15% EtOAc/DCM)

Sources & evidence

ORD record
ord-403d6361ce314f8ebccfbe00e20725f0
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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