Ethylene Glycol → HCID 21106524, compound

HRID 1765382Notes

Reaction equation

HRID 1765382 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.[CH3:20][C:21]([S-:24])([CH3:23])[CH3:22].[Na+].C(O)CO.O>CN1CCCC1=O.[Cu]I>[C:21]([S:24][C:16]1[CH:17]=[CH:18][C:13]([N:4]2[NH:3][C:2](=[O:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]2=[O:12])=[CH:14][CH:15]=1)([CH3:23])([CH3:22])[CH3:20]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 5147913Sodium 2-methyl-2-propanethiolateHCID 178515031HCID 178515031, compound

Product 1

HCID 21106524HCID 21106524, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

4-Hydroxy-2-(4-iodophenyl)-2H-phthalazin-1-one (see Method Q) (0.30 g, 0.8 mmol), sodium 2-methyl-propane-2-thiolate (0.094 g, 0.8 mmol), CuI (0.011 g, 0.06 mmol) and ethylene glycol (0.10 g, 1.6 mmol) were dissolved in N-methyl-pyrrolidinone (NMP) (0.5 ml) under argon and heated to 150° C. Stirring at this temperature was continued for 4 d before the mixture was allowed to warm to room temperature. H2O (50 ml) was added and the precipitated solid was collected by filtration. The title compound was obtained after purification of the raw product by chromatography over silica gel with dichloromethane (0.21 g, 78%). 1H-NMR: (400 MHz, D6-DMSO) 12.35 (1H, s), 8.73 (1H, d), 8.33–8.41 (3H, m), 8.14 (2H, d), 8.01 (2H, d), 1.70 (9H, s); MS (ESI+)=327.14 (M+H)+.

Workup

  1. temperatureto warm to room temperature
  2. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-0be4f6148b614e8c936d6906356c5fb9
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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