Triethylamine → (E)-1-cinnamyl-3-(3-pyridyl)imidazolidine-2-thione

HRID 477001Notes

Reaction equation

HRID 477001 reaction equation
[CH2:1]([NH:10][CH2:11][CH2:12][NH:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:27](Cl)(Cl)=[S:28]>O1CCCC1>[CH2:1]([N:10]1[CH2:11][CH2:12][N:13]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C:27]1=[S:28])/[CH:2]=[CH:3]/[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 14834214(E)-N-cinnamyl-N'-(3-pyridyl)ethylenediamine

Product 1

HCID 14834215(E)-1-cinnamyl-3-(3-pyridyl)imidazolidine-2-thioneYield 45.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5.37 g of (E)-N-cinnamyl-N'-(3-pyridyl)ethylenediamine dissolved in 100 ml of tetrahydrofuran, 4.5 g of triethylamine was added and the mixture was ice-cooled. To the mixture was added dropwise 20 ml of a tetrahydrofuran solution containing 5.12 g of thiophosgene over 5 minutes, and subsequently the mixture was stirred under ice-cooling for 30 minutes and then at room temperature for 2 hours. The solvent was distilled off, and the residue was dissolved in chloroform, washed with water and dried, followed by distillation of the solvent. The residue was purified by silica gel column chromatorgraphy (solvent: chloroform-methanol=20:1) to give 2.86 g of (E)-1-cinnamyl-3-(3-pyridyl)imidazolidine-2-thione as caramel.

Workup

  1. temperaturecooled
  2. temperaturecooling for 30 minutes
  3. distillationThe solvent was distilled off
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed with water
  6. customdried
  7. distillationfollowed by distillation of the solvent
  8. customThe residue was purified by silica gel column chromatorgraphy (solvent: chloroform-methanol=20:1)

Sources & evidence

ORD record
ord-4e1d32d67184480d8caeb5e852673a2b
Source dataset
uspto-grants-1989_12
Patent number
US04886817

Reaction notes

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