Methyl iodide → HCID 178488069, compound

HRID 1885218Notes

Reaction equation

HRID 1885218 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 mmols). 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 C15H14N2O2O2S2 :

Workup

  1. filtrationFiltration
  2. washwashing with ether

Sources & evidence

ORD record
ord-e6461d467e2b46439b58b8510245e906
Source dataset
uspto-grants-1992_09
Patent number
US05143927

Reaction notes

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