1,1'-Thiocarbonyldiimidazole → 1-(4-Chloro-2-methyl-phenyl)-3-ethyl-3,4,5,6-tetrahydro-primidine-2(1H)-thione

HRID 1250878Notes

Reaction equation

HRID 1250878 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH3:14])=[C:4]([CH3:15])[CH:3]=1.[C:16](N1C=CN=C1)(N1C=CN=C1)=[S:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[C:16]2=[S:17])=[C:4]([CH3:15])[CH:3]=1

Participants

5

Reactant 3

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 521998p-Toluenesulfonic acid monohydrateHCID 18324839N'-(4-Chloro-2-methyl-phenyl)-N-ethyl-propane-1,3-diamine

Product 1

HCID 101992671-(4-Chloro-2-methyl-phenyl)-3-ethyl-3,4,5,6-tetrahydro-primidine-2(1H)-thione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The cyclization of the crude diamine of Step D was carried out with one equivalent of 1,1′-thiocarbonyldiimidazole in refluxing dioxane under nitrogen for one hour. Subsequently, two equivalents of para-toluenesulfonic acid hydrate were added and the mixture was refluxed for 48 hours. The solvent was removed in vacuo and the residue was dissolved in dichloromethane (100 mL). The solution was washed with water, dried over magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography (on Merck-60 silica gel) eluting with 10-25% petroleum ether/ethyl acetate. The title compound was obtained as a white solid (4.4 g, 52%), m.p. 116-118° C.

Workup

  1. temperaturethe mixture was refluxed for 48 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane (100 mL)
  4. washThe solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash chromatography (on Merck-60 silica gel)
  9. washeluting with 10-25% petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-aaa4c8eacb29455d879c962c22dad28e
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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