Methyl iodide → HCID 12146788, compound

HRID 29025Notes

Reaction equation

HRID 29025 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[CH2:5][N:6]=[C:7]1[N:12]=[CH:11][C:10]([CH3:14])([CH3:13])[CH2:9][S:8]1.[C:19](=[S:21])=[S:20].[H-].[Na+].[CH3:24]I>O.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[CH2:5][N:6]=[C:7]1[N:12]([C:19]([S:21][CH3:24])=[S:20])[CH2:11][C:10]([CH3:14])([CH3:13])[CH2:9][S:8]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 22639986HCID 22639986, compound

Product 1

HCID 12146788HCID 12146788, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(2-methoxybenzyl)imino-5,5-dimethyl-1,3-thiazine (0.27 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. Methyl iodide (0.17 g) was added thereto. The mixture was stirred at room temperature for 2 hours. To the solution 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-methoxybenzyl)imino-3-(methylthio)thiocarbonyl-5,5-dimethyl-1,3-thiazine (0.20 g, yield: 57%) 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-ae8d4ebe42fc4dbbb068fd1ee90b2d0d
Source dataset
uspto-grants-2008_09
Patent number
US07420053B2

Reaction notes

Loading…