Methyl iodide → HCID 20458824, compound

HRID 544378Notes

Reaction equation

HRID 544378 reaction equation
[CH3:1][C:2]1([CH3:8])[NH:6][C:5](=[S:7])[CH2:4][S:3]1.[Na].[H][H].[CH3:12]I>CN(C)C=O>[CH3:1][C:2]1([CH3:8])[N:6]=[C:5]([S:7][CH3:12])[CH2:4][S:3]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 5360545SodiumHCID 20458836HCID 20458836, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20458824HCID 20458824, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

6.0 g (0.041 mol) of 2,2-dimethyl-thiazolidine-4-thione are added cautiously to a suspension of 1.0 g (0.041 mol) of oil-free sodium hydridein 20 ml of absolute dimethylformamide. After completion of the evolution of hydrogen, the mixture is heated briefly to 50° C., then cooled to 0° C. and 2.6 ml (0.042 mol) of methyl iodide are added dropwisethereto. After removing the ice-bath the mixture is stirred for an additional 3 hours, treated with water and extracted twice with methylene chloride. The organic extracts are subsequently combined, washed three times with 100 ml of water each time, dried over anhydrous sodium sulfate and evaporated at 40° C. under reduced pressure to yield crude 2,2-dimethyl-4-methylthio-3-thiazoline.

Workup

  1. customAfter removing the ice-bath the mixture
  2. additiontreated with water
  3. extractionextracted twice with methylene chloride
  4. washwashed three times with 100 ml of water each time
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-1be09dcb0fe44eb7a6fca165733e792c
Source dataset
uspto-grants-1984_05
Patent number
US04450157

Reaction notes

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