Methyl iodide → HCID 54541284, compound

HRID 1660524Notes

Reaction equation

HRID 1660524 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>CN(C)C=O.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 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 54541284HCID 54541284, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

17.5 g of cis-4,5-diphenyl-imidazolidine-2-thione are dissolved in 200 ml of dimethylformamide and first a solution of 3.2 g of sodium hydroxide in 20 ml of water and then 11.6 g of methyl iodide are added. The mixture is stirred for 6.5 hours at room temperature and evaporated to dryness, the residue is stirred with 350 ml of water and, after leaving to stand for some time, the mixture is filtered with suction, the solid material from the mixture is dissolved, whilst still moist, in 350 ml of ethanol and 50 ml of 2 N sodium hydroxide solution and 170 ml of water are added. The crystalline precipitate is filtered off with suction, filtered through silica gel using chloroform as the eluant and recrystallised from isopropanol/petroleum ether. cis-2-Methylthio-4,5-diphenyl-imidazoline with a melting point of 132°-134° is obtained.

Workup

  1. customevaporated to dryness
  2. stirringthe residue is stirred with 350 ml of water
  3. customafter leaving
  4. filtrationthe mixture is filtered with suction
  5. dissolutionthe solid material from the mixture is dissolved
  6. additionwhilst still moist, in 350 ml of ethanol and 50 ml of 2 N sodium hydroxide solution and 170 ml of water are added
  7. filtrationThe crystalline precipitate is filtered off with suction
  8. filtrationfiltered through silica gel
  9. customrecrystallised from isopropanol/petroleum ether

Sources & evidence

ORD record
ord-80230a9f9b1e43b684098d5f2822e485
Source dataset
uspto-grants-1981_12
Patent number
US04308277

Reaction notes

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