1,1'-Thiocarbonyldiimidazole → 2(1H)-Pyrimidinethione, tetrahydro-1-phenyl-

HRID 1250876Notes

Reaction equation

HRID 1250876 reaction equation
[C:1]1([NH:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12](N1C=CN=C1)(N1C=CN=C1)=[S:13]>ClCCl>[C:1]1([N:7]2[CH2:8][CH2:9][CH2:10][NH:11][C:12]2=[S:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 427260N-(3-aminopropyl)aniline

Product 1

HCID 101980352(1H)-Pyrimidinethione, tetrahydro-1-phenyl-Yield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared in the manner of Example 1, Step B from N-phenyl-propane-1,3-diamine of Step A and 1,1′-thiocarbonyldiimidazole, except that the cyclization was effected in dichloromethane. Workup consisted of washing with water, drying over magnesium sulfate, filtration and removal of solvent in vacuo. Purfication by flash chromatography on silica gel Merck-60 eluting with 1% methanol in dichloromethane followed by trituration with ethyl ether to provide the title compound as a white solid (2.74 g, 78%), m.p: 211-212° C., identical to the material described by Kashima et al., J. Chem. Soc. Perkin I, 1622 (1981).

Workup

  1. washof washing with water
  2. dry with materialdrying over magnesium sulfate, filtration and removal of solvent in vacuo
  3. washeluting with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-1b0acefd610e43ee866e404e4b3a2777
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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