Methyl iodide → HCID 677048, compound

HRID 425765Notes

Reaction equation

HRID 425765 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[C:11]3[S:15][C:14](=[S:16])[NH:13][C:12]3=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:18]CN(C(C)C)C(C)C.CI.CCOC(C)=O>CN1C(=O)CCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[C:11]3[S:15][C:14]([S:16][CH3:18])=[N:13][C:12]3=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 2785114HCID 2785114, compound

Product 1

HCID 677048HCID 677048, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

2 g (7.54 mmol) of 5-Benzo[1,3]dioxol-5-ylmethylene-2-thioxo-thiazolidin-4-one and 1.5 ml (1.15 eq.) of DIEA were dissolved in 80 ml NMP. To this solution was added dropwise a freshly prepared solution of 2.43 ml (5 eq.) of Methyliodide in 10 ml NMP. The reaction mixture was stirred for two hours at RT. EtOAc was added and the organic layer was washed 5 times with brine and twice with water. The organic layer was reduced to 50% of volume, where upon 5-Benzo[1,3]dioxol-5-ylmethylene-2-methylsulfanyl-thiazol-4-one started to crystallize. Crystals were filtered off and washed with cold EtOAc.

Workup

  1. washthe organic layer was washed 5 times with brine
  2. customto crystallize
  3. filtrationCrystals were filtered off
  4. washwashed with cold EtOAc

Sources & evidence

ORD record
ord-7e2bc4424cc54bdb86555256b3ac7c90
Source dataset
uspto-grants-2012_01
Patent number
US08106214B2

Reaction notes

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