Methyl iodide → HCID 178503444, compound

HRID 1702143Notes

Reaction equation

HRID 1702143 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:6][NH:5][C:4](=[S:7])[NH:3]1.[CH3:9][I:10]>C(O)(C)C.CCOCC>[IH:10].[CH3:1][C:2]1([CH3:8])[CH2:6][NH:5][C:4]([S:7][CH3:9])=[N:3]1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 30325022-Imidazolidinethione, 4,4-dimethyl-

Product 1

HCID 178503444HCID 178503444, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

A suspension of 110 g (0.83 M) of 4,4-dimethyl-2-imidazolidinethione in 700 ml isopropanol was treated with 148 g (1.04 M) methyl iodide and stirred at room temperature under reflux for 1/2 hour. When all had dissolved, heated to gentle reflux for 1 hour. Cool, dilute to 2 liters with anhydrous ether, seed, and cool in ice. Filter and wash with dry ether. Yield of 4,4-dimethyl-2-(methylthio)imidazoline hydroiodide was 221 g, 98%, mp 93.5°-95° C. Pure material melts at 94.5°-95° C.

Workup

  1. temperatureunder reflux for 1/2 hour
  2. dissolutionWhen all had dissolved
  3. temperatureheated
  4. temperatureto gentle reflux for 1 hour
  5. temperatureCool
  6. temperaturecool in ice
  7. filtrationFilter
  8. washwash with dry ether

Sources & evidence

ORD record
ord-7fa741dc452a4a979ee62a3c1ed6ffb7
Source dataset
uspto-grants-1983_04
Patent number
US04380548

Reaction notes

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