Acetoin → 1,3,4,5-Tetramethyl-1,3-dihydro-2H-imidazole-2-thione

HRID 1358898Notes

Reaction equation

HRID 1358898 reaction equation
[CH3:1][NH:2][C:3](=[S:6])[NH:4][CH3:5].O[CH:8]([CH3:12])[C:9](=O)[CH3:10]>C(O)CCCCC>[CH3:1][N:2]1[C:9]([CH3:10])=[C:8]([CH3:12])[N:4]([CH3:5])[C:3]1=[S:6]

Participants

4

Reactant 2

HCID 179AcetoinHCID 2723631N,N'-Dimethylthiourea

Product 1

HCID 125032871,3,4,5-Tetramethyl-1,3-dihydro-2H-imidazole-2-thione

Reagents, catalysts & solvents 1

HCID 81031-HexanolSolvent2×

Conditions

Temperature
155 °C

Procedure

1,3-dimethyl-4,5-dimethylimidazole-2-thione was synthesized according to a method obtained by modifying a method suggested by N. Kuhn, et al. (N. Kuhn and T. Kratz, Synthesis, June 1993, p.561), and a procedure of synthesizing the same is described below. 100 mmol of dimethylthiourea and 100 mmol of 3-hydroxyl-2-butanone were added to 250 ml of 1-hexanol in order, and then subjected to a reflux reaction for about 12 hours while increasing a reaction temperature to 150 to 160° C. At this time, white solid reactants were dissolved in 1-hexanol to be partly converted into yellow solid reactants according to an increase in the reaction temperature. After a completion of the reflux reaction, the resulting solution was left in a freezer at about −30° C. for about one day to separate into a white solid component and a yellow liquid component. The yellow liquid component was removed by use of a syringe, and the remaining white solid component was rinsed with water and ether and dried to produce 1,3-dimethyl-4,5-dimethylimidazole-2-thione. 1,3-dimethyl-4,5-dimethylimidazole-2-thione thus produced was analyzed by a 1H-NMR analyzer and the results are as follows:

Workup

  1. custom1,3-dimethyl-4,5-dimethylimidazole-2-thione was synthesized
  2. customobtained
  3. customKuhn, et al. (N. Kuhn and T. Kratz, Synthesis, June 1993, p.561)
  4. customa procedure of synthesizing the
  5. customsubjected to a reflux reaction for about 12 hours
  6. temperaturean increase in the reaction temperature
  7. customAfter a completion of the reflux reaction
  8. customto separate into a white solid component
  9. customThe yellow liquid component was removed by use of a syringe
  10. washthe remaining white solid component was rinsed with water and ether
  11. customdried

Sources & evidence

ORD record
ord-daa52c4d344d446f9f4fd07de2e399de
Source dataset
uspto-grants-2003_07
Patent number
US06599587B2

Reaction notes

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