Water → HCID 54200171, compound

HRID 1660525Notes

Reaction equation

HRID 1660525 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[NH:12][C:11](=[S:22])[NH:10]2)=[CH:5][CH:4]=1.[Na].[CH2:24](I)[CH3:25].O>CO.CN(C)C=O>[CH2:24]([S:22][C:11]1[NH:12][C@H:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C@H:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1)[CH3:25]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 5360545SodiumHCID 22821809HCID 22821809, compound

Product 1

HCID 54200171HCID 54200171, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

12 g of cis-4,5-bis-(p-methoxyphenyl)-imidazolidine-2-thione are added to a solution of 0.88 g of sodium in 13 ml of methanol. The mixture is then diluted with 200 ml of dimethylformamide and left to stand overnight, 4 ml of ethyl iodide are added and the mixture is stirred for 5 hours at room temperature and poured into 300 ml of water. The crystals which have precipitated out are filtered off with suction and dissolved in methylene chloride. The solution is dried over sodium sulfate and evaporated and the residue is dissolved in acetone. The acetone solution is rendered weakly acid with methanolic hydrochloric acid (4.5μ) and the cis-2-ethylthio-4,5-bis-(p-methoxyphenyl)-imidazoline hydrochloride which has precipitated is filtered off. In order to liberate the base, this hydrochloride is treated with 2 N sodium hydroxide solution and the crude base is then rcrystallised from isopropanol/petroleum ether. cis-2-Ethylthio-4,5-bis-(p-methoxyphenyl)-imidazoline with a melting point of 92°-93° is obtained.

Workup

  1. waitleft
  2. customThe crystals which have precipitated out
  3. filtrationare filtered off with suction
  4. dissolutiondissolved in methylene chloride
  5. dry with materialThe solution is dried over sodium sulfate
  6. customevaporated
  7. dissolutionthe residue is dissolved in acetone
  8. customthe cis-2-ethylthio-4,5-bis-(p-methoxyphenyl)-imidazoline hydrochloride which has precipitated
  9. filtrationis filtered off
  10. additionthis hydrochloride is treated with 2 N sodium hydroxide solution

Sources & evidence

ORD record
ord-50ff078100d44a55a57f9b6de8e7a603
Source dataset
uspto-grants-1981_12
Patent number
US04308277

Reaction notes

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