Ethylene Glycol → HCID 21106520, compound

HRID 1765384Notes

Reaction equation

HRID 1765384 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-iodophenyl)-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 room temperature. H2O (50 ml) was added and the resulting solution was extracted with dichloromethane. The title compound was obtained after purification of the raw product by chromatography over silica gel with dichloromethane (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 room temperature
  2. extractionthe resulting solution was extracted with dichloromethane

Sources & evidence

ORD record
ord-d8b42f63f48540038024969ec6071e2e
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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