1,1'-Thiocarbonyldiimidazole → 1-[2-(1-Adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)propyl]thiourea

HRID 11468Notes

Reaction equation

HRID 11468 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.[C:11](N1C=CN=C1)(N1C=CN=C1)=[S:12].Cl.[C:24]12([CH2:34][CH2:35][NH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[C:24]12([CH2:34][CH2:35][N:36]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:11]([NH:1][CH2:2][CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=3)=[S:12])[CH2:31][CH:30]3[CH2:29][CH:28]([CH2:27][CH:26]([CH2:32]3)[CH2:25]1)[CH2:33]2

Participants

7

Reactant 4

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 143474663-(Pyridin-4-yl)propan-1-amineHCID 498316802-(1Adamantyl)-n-pentylethylamine hydrochloride

Product 1

HCID 219739841-[2-(1-Adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)propyl]thioureaYield 24%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(3-aminopropyl)pyridine (Intermediate No. 2-1) (0.24 g, 1.8 mmol) in anhydrous tetrahydrofuran (10 ml) was added to 1,1′-thiocarbonyldiimidazole (0.31 g, 1.8 mmol) under a nitrogen atmosphere, and the mixture was stirred at room temperature. After one hour, a solution of 2-(1-adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1) (0.50 g, 1.8 mmol) in anhydrous tetrahydrofuran (10 ml) was added to the mixture, and the whole was refluxed for 2.5 hours. The reaction mixture was allowed to stand, then ethyl acetate (50 ml) and a saturated aqueous sodium hydrogencarbonate solution (50 ml) were added to the reaction mixture, and layers were separated. The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution (50 ml) and dried over anhydrous magnesium sulfate. The ethyl acetate layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to give 0.18 g (24%) of the titled compound.

Workup

  1. temperaturethe whole was refluxed for 2.5 hours
  2. customwere separated
  3. washThe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe ethyl acetate layer was concentrated under reduced pressure
  6. customthe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1a9c8bf2a0c94a929282d4054ef2be97
Source dataset
uspto-grants-2006_08
Patent number
US07098226B2

Reaction notes

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