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

HRID 1250880Notes

Reaction equation

HRID 1250880 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:15])=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH3:14])[CH:7]=1.[C:16](N1C=CN=C1)(N1C=CN=C1)=[S:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:15])=[C:6]([N:8]2[CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[C:16]2=[S:17])[CH:7]=1

Participants

6

Reactant 3

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 521998p-Toluenesulfonic acid monohydrateHCID 18324842N'-(5-Chloro-2-methyl-phenyl)-N-ethyl-propane-1,3-diamine

Product 1

HCID 98818621-(5-Chloro-2-methyl-phenyl)-3-ethyl-3,4,5,6-tetrahydro-pyrimidine-2(1H)-thioneYield 25%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of the diamine of Step A (7.1 g) in dioxane (250 mL) and 1,1′-thiocarbonyldiimidazole (5.6 g) was refluxed under nitrogen for 2.5 hrs. Following the addition of para-toluenesulfonic acid monohydrate (11.9 g), the reaction mixture was heated at reflux for 48 hrs. The reaction was cooled and filtered and the filtrate was concentrated in vacuo to give a brown oil. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with 20% ethyl acetate in hexane provided a brown solid which was triturated with diethyl ether to give the title product (2.1 g, 25.0%) as a white solid, m.p. 111-112° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 48 hrs
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give a brown oil
  7. customabsorbed onto a column of Merck-60 flash silica gel
  8. washElution with 20% ethyl acetate in hexane
  9. customprovided a brown solid which
  10. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-99fc24dbde584f5b8d2b5a92d9841fc5
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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