Triethylamine → 1-Adamantan-2-yl-3-(4-methoxy-2-methyl-phenyl)-urea

HRID 1259030Notes

Reaction equation

HRID 1259030 reaction equation
Cl.[CH:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[NH2:12])[CH2:9]2.C(N(CC)CC)C.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[C:24]([CH3:31])[CH:23]=1>C(O)C>[CH:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[NH:12][C:29]([NH:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][C:24]=1[CH3:31])=[O:30])[CH2:9]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 253312-Aminoadamantane hydrochlorideHCID 27349054-Methoxy-2-methylphenyl isocyanate

Product 1

HCID 161268821-Adamantan-2-yl-3-(4-methoxy-2-methyl-phenyl)-ureaYield 100.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.5 g (13.3 mmol) of 2-adamantylamine hydrochloride, 1.84 ml (13.3 mmol) of triethylamine in 50 ml of ethanol was heated under reflux. Then 1.94 ml (13.3 mmol) of 4-methoxy-2-methylphenylisocyanate was added and the mixture was stirred under reflux for 2 h. After cooling at room temperature the precipitate was filtered, washed with ethanol and dried under vacuum to give 4.2 g (61%) a white solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureunder reflux for 2 h
  4. filtrationwas filtered
  5. washwashed with ethanol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-dddcad61240d49dd85befb42c99b307f
Source dataset
uspto-grants-2013_06
Patent number
US08466200B2

Reaction notes

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