Methyl iodide → HCID 68571092, compound

HRID 1660522Notes

Reaction equation

HRID 1660522 reaction equation
[C:1]1([C@H:7]2[C@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:10][C:9](=[S:18])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH3:21]I>CO.O>[CH3:21][S:18][C:9]1[NH:8][C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C@H:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 11010529HCID 11010529, compound

Product 1

HCID 68571092HCID 68571092, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1.8 g of trans-4,5-diphenyl-imidazolidine-2-thione are dissolved in 20 ml of methanol, a solution of 0.3 g of sodium hydroxide in 2 ml of water and also 1.2 g of methyl iodide are added and the mixture is stirred at room temperature for 4 hours and left to stand overnight at 0°. The reaction mixture is evaporated to dryness, the residue is shaken with a mixture of 40 ml of water and 40 ml of ethyl acetate, the organic phase is separated off and the aqueous phase is washed with ethyl acetate. The organic phases are dried over sodium sulfate and evaporated to dryness. The crystalline residue is recrystallised, first from methanol and then from a mixture of diethyl ether and petroleum ether. Trans-2-methylthio-4,5-diphenyl-imidazoline with a melting point of 135°-137° is obtained.

Workup

  1. waitleft
  2. waitto stand overnight at 0°
  3. customThe reaction mixture is evaporated to dryness
  4. stirringthe residue is shaken with a mixture of 40 ml of water and 40 ml of ethyl acetate
  5. customthe organic phase is separated off
  6. washthe aqueous phase is washed with ethyl acetate
  7. dry with materialThe organic phases are dried over sodium sulfate
  8. customevaporated to dryness
  9. customThe crystalline residue is recrystallised, first from methanol
  10. additionfrom a mixture of diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-3ffe3a62e79947d0bcee100a0a2f9a94
Source dataset
uspto-grants-1981_12
Patent number
US04308277

Reaction notes

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