Methyl iodide → 2-(2-Isopropylphenyl)imino-3-(methylthio)thiocarbonyl-1,3-thiazolidine

HRID 29023Notes

Reaction equation

HRID 29023 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[C:11]1[NH:15][CH2:14][CH2:13][S:12]1)([CH3:3])[CH3:2].[C:16](=[S:18])=[S:17].[H-].[Na+].[CH3:21]I>O.CN(C)C=O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[C:11]1[N:15]([C:16]([S:18][CH3:21])=[S:17])[CH2:14][CH2:13][S:12]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 178438962HCID 178438962, compound

Product 1

HCID 121467842-(2-Isopropylphenyl)imino-3-(methylthio)thiocarbonyl-1,3-thiazolidineYield 45.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(2-isopropylphenyl)imino-1,3-thiazolidine (0.22 g), carbon disulfide (0.09 g) and N,N-dimethylformamide (2 ml) was added under ice-cooling 60% sodium hydride (0.05 g). The mixture was stirred for 30 minutes. Methyliodide (0.17 g) was added thereto. The mixture was stirred at room temperature for 2 hours. To the mixture was added water (30 ml). The mixture was extracted with diethylether (60 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to give 2-(2-isopropylphenyl)imino-3-(methylthio)thiocarbonyl-1,3-thiazolidine (0.14 g, yield: 45%) as colorless oil.

Workup

  1. additionwas added under ice-
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. extractionThe mixture was extracted with diethylether (60 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e61a2fa3cd494a25b434c12a6b24cd7b
Source dataset
uspto-grants-2008_09
Patent number
US07420053B2

Reaction notes

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