Iodoethane → HCID 54351304, compound

HRID 1660526Notes

Reaction equation

HRID 1660526 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.[CH2:19](I)[CH3:20]>CO>[CH2:19]([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)[CH3:20]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 54351304HCID 54351304, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

10.3 g of cis-4,5-diphenyl-imidazolidine-2-thione are suspended in a mixture of 25 ml of methanol and 3.8 ml of ethyl iodide and the suspension is refluxed for 1 hour, with stirring. A further 75 ml of methanol are then added and the mixture is refluxed for 16 hours. The clear reaction solution is evaporated to dryness and the residue is taken up in a mixture of 150 ml of water and 250 ml of ethyl acetate. In order to liberate the base, the mixture is rendered alkaline iwth concentrated aqueous ammonia solution and shaken thoroughly and the organic phase is separated off, dried over sodium sulfate and evaporated. Recrystallisation of the residue from isopropanol/petroleum ether yields cis-2-ethylthio-4,5-diphenyl-imidazoline with a melting point of 95°-96°.

Workup

  1. temperaturethe suspension is refluxed for 1 hour
  2. temperaturethe mixture is refluxed for 16 hours
  3. customThe clear reaction solution is evaporated to dryness
  4. additionthe residue is taken up in a mixture of 150 ml of water and 250 ml of ethyl acetate
  5. stirringshaken thoroughly
  6. customthe organic phase is separated off
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customRecrystallisation of the residue from isopropanol/petroleum ether

Sources & evidence

ORD record
ord-8c44505bdb1749319267c078524b302d
Source dataset
uspto-grants-1981_12
Patent number
US04308277

Reaction notes

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