Methyl iodide → 4-Ethoxy-6-[2-methylsulfanyl-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-quinoline-3-carbonitrile

HRID 1297633Notes

Reaction equation

HRID 1297633 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](/[CH:14]=[C:15]3/[C:16](=[O:21])[NH:17][C:18](=[S:20])[S:19]/3)[CH:12]=2)[N:7]=[CH:6][C:5]=1[C:22]#[N:23])[CH3:2].IC.[CH:26](N(C(C)C)CC)(C)C.CCCCCC>C(O)C>[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](/[CH:14]=[C:15]3/[C:16](=[O:21])[N:17]=[C:18]([S:20][CH3:26])[S:19]/3)[CH:12]=2)[N:7]=[CH:6][C:5]=1[C:22]#[N:23])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 81531DiisopropylethylamineHCID 585857804-ethoxy-6-[4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile

Product 1

HCID 585858204-Ethoxy-6-[2-methylsulfanyl-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-quinoline-3-carbonitrileYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the suspension of 4-ethoxy-6-[4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile (example 14f) (1.7 g, 5 mmol), iodomethane (0.62 mL, 10 mmol) and DIEA (diisopropylethylamine) (1.7 mL, 10 mmol) in anhydrous ethanol (25 mL) was stirred at room temperature for 24 h. After adding hexane (50 mL), the solid was collected by filtration, washed with hexane and dried. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 0%-5% methanol in methylene chloride in 30 min) afforded to obtain 4-ethoxy-6-[2-methylsulfanyl-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile(1.25 g, 75%) as a yellow solid. LC-MS m/e 356 (MH+)

Workup

  1. filtrationthe solid was collected by filtration
  2. washwashed with hexane
  3. customdried
  4. customFlash chromatography (Merck Silica gel 60, 230-400 mesh, 0%-5% methanol in methylene chloride in 30 min) afforded

Sources & evidence

ORD record
ord-3804f775599847778112c9a914d62278
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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