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

HRID 18404Notes

Reaction equation

HRID 18404 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, and then ethyl acetate (50 ml) and a saturated aqueous sodium hydrogencarbonate solution (50 ml) were added to the reaction mixture. After separation, the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution (50 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Then the obtained concentrate was purified by silica gel column chromatography to give the target compound (0.18 g, 24%).

Workup

  1. temperaturethe whole was refluxed for 2.5 hours
  2. customAfter separation
  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. concentrationconcentrated under reduced pressure
  6. concentrationThen the obtained concentrate
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7d6bbac54772480faccb9f24ab8a02a6
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Reaction notes

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