Methyl iodide → HCID 178503539, compound

HRID 1655397Notes

Reaction equation

HRID 1655397 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[C:12]1[S:16][C:15](=[S:17])[NH:14][C:13]1=[O:18])=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:19]CN(C(C)C)C(C)C.IC>CO>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[C:12]1[S:16][C:15]([S:17][CH3:19])=[N:14][C:13]1=[O:18])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178433615HCID 178433615, compound

Product 1

HCID 178503539HCID 178503539, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a room temperature suspension of (Z) 5-[(2-methyl-1H-indol-3-yl)methylene]-2-thioxo-4-thiazolidinone (1.502 g, 5.48 mmols) in 50 mL of methanol is added Hunig's base (1.15 mL, 6.61 mmols) followed by iodomethane (0.500 mL, 8.03 mmols). The thick suspension is stirred for 2 hours at room temperature. Filtration washing with 1:1 hexane:ether provides 1.201 g of an orange solid. This material is suspended in 100 mL of hot ethyl acetate and filtered to provide 943 mg (60%) of (Z)-5-[(2-methyl-1H-indol-3-yl)methylene]-2-(methylthio)-4(5H)-thiazolone; mp 253-255° C. dec.

Workup

  1. filtrationFiltration
  2. washwashing with 1:1 hexane

Sources & evidence

ORD record
ord-1a1fa1b1310948038b69e0f95d01a67a
Source dataset
uspto-grants-1993_10
Patent number
US05250552

Reaction notes

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