Methyl iodide → HCID 178488069, compound

HRID 1655395Notes

Reaction equation

HRID 1655395 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2/[CH:13]=[C:14]1/[C:15](=[O:20])[NH:16][C:17](=[S:19])[S:18]/1.[CH3:21]CN(C(C)C)C(C)C.IC>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2/[CH:13]=[C:14]1/[C:15](=[O:20])[N:16]=[C:17]([S:19][CH3:21])[S:18]/1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178488071HCID 178488071, compound

Product 1

HCID 178488069HCID 178488069, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a room temperature suspension of (Z)-5-[(5-methoxy-2 methyl-1H-indol-3-yl)methylene]-2-thioxo-4-thiazolidinone (1.714 g, 5.63 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 nmmols). The thick suspension is stirred overnight at room temperature. Filtration washing with ether provides 1.631 g (91%) of (Z)-5-[(5-methoxy-2-methyl-1H-indol-3-yl)methylene]-2(methylthio)-4(5H) thiazolone; mp 214-222° C. dec. Calc'd for C15H14N2O2S2 :

Workup

  1. filtrationFiltration
  2. washwashing with ether

Sources & evidence

ORD record
ord-6f2b3b5e3de94d07bb2d645407a6758d
Source dataset
uspto-grants-1993_10
Patent number
US05250552

Reaction notes

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