Ethylene Glycol → HCID 21106520, compound

HRID 1783697Notes

Reaction equation

HRID 1783697 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=2)[N:3]=1.[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)CO.O>CN1CCCC1=O.[Cu]I>[C:20]1([S:26][C:16]2[CH:17]=[CH:18][C:13]([N:4]3[NH:3][C:2](=[O:1])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]3=[O:12])=[CH:14][CH:15]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 7969ThiophenolHCID 178515031HCID 178515031, compound

Product 1

HCID 21106520HCID 21106520, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

4-Hydroxy-2-(4-iodo-phenyl)-2H-phthalazin-1-one (see Method Q) (0.20 g, 0.55 mmol), thiophenol (0.061 g, 0.55 mmol), CuI (0.006 g, 0.03 mmol) and ethylene glycol (0.070 g, 1.1 mmol) were dissolved in N-methyl-pyrrolidinone (NMP) (1 ml) under argon and heated to 90° C. Stirring at this temperature was continued for 26 h before the mixture was allowed to warm to RT. H2O (50 ml) was added and the resulting solution was extracted with DCM. The title compound was obtained after purification of the raw product by chromatography over silica gel with DCM (0.10 g, 54%). 1H-NMR: (400 MHz, D6-DMSO) 11.91 (1H, s), 8.30 (1H, s), 7.91-8.06 (3H, m), 7.69 (2H, d), 7.34-7.45 (7H, m); MS (ESI+)=347.26 (M+H)+.

Workup

  1. temperatureto warm to RT
  2. extractionthe resulting solution was extracted with DCM

Sources & evidence

ORD record
ord-fd6aee5fbb5e4233b94f6c26b29e4c9b
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

Loading…