Methyl iodide → (Z)-5-[[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]methylene]-2-(methylthio)-4(5 H)-thiazolone

HRID 1885229Notes

Reaction equation

HRID 1885229 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[C:18]1/[C:19](=[O:24])[NH:20][C:21](=[S:23])[S:22]/1.[CH3:25]CN(C(C)C)C(C)C.IC>C(O)C>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[C:18]1/[C:19](=[O:24])[N:20]=[C:21]([S:23][CH3:25])[S:22]/1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 9822030(Z)-5-[[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]methylene]-2-thioxo-4-thiazolidinone

Product 1

HCID 19880349(Z)-5-[[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]methylene]-2-(methylthio)-4(5 H)-thiazoloneYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To room temperature suspension of (Z)-5-[[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]methylene]-2-thioxo-4-thiazolidinone (3.177 g, 8.04 mmols) in 125 mL of ethanol is added Hunig's base (1.57 mL, 9.03 mmols) followed by iodomethane (600 μL, 9.63 mmols). After stirring at room temperature overnight the yellow solid is collected by filtration to give 2.861 g (87%) of (Z)-5-[[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]methylene]-2-(methylthio)-4(5 H)-thiazolone. An analytical sample is obtained by recrystallization from hexane-ethyl acetate; mp 233°-236° C. Calc'd for C18H14Cl2N2OS2:

Workup

  1. filtrationis collected by filtration

Sources & evidence

ORD record
ord-3aaef7d006404b32a4e65811012ee65e
Source dataset
uspto-grants-1992_09
Patent number
US05143929

Reaction notes

Loading…