Ethanol → [4-(2-Hydroxy-2-phenyl-propyl)-pyridin-2-yl]-urea

HRID 1023430Notes

Reaction equation

HRID 1023430 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([OH:11])[CH3:10])[CH:5]=[CH:4][N:3]=1.[C:18]([N:26]=C=O)(=[O:25])C1C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[OH:11][C:9]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([CH3:10])[CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:18]([NH2:26])=[O:25])[CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 64128755HCID 64128755, compound

Product 1

HCID 69081585[4-(2-Hydroxy-2-phenyl-propyl)-pyridin-2-yl]-ureaYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

The crude 1-(2-Amino-pyridin-4-yl)-2-phenyl-propan-2-ol (120 mg) is dissolved in methylene chloride (4 mL). Then benzoyl isocynate (155 mg, 1.1 mmol) is added. The reaction mixture is sealed and heated at 50° C. for 16 hour. The solvent is then carefully removed and to the residue are added ethanol (5 mL) and potassium carbonate (73 mg, 0.53 mmol). The resulting mixture is heated at 85° C. for 2 hrs. Then solvent is removed to give the crude product which is purified by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) to give 67 mg of the titled product.

Workup

  1. customThe reaction mixture is sealed
  2. customThe solvent is then carefully removed and to the residue
  3. temperatureThe resulting mixture is heated at 85° C. for 2 hrs
  4. customThen solvent is removed
  5. customto give the crude product which
  6. customis purified by silica flash column chromatography

Sources & evidence

ORD record
ord-e08c1eca57ef4629b2d74b8ed1ba55a7
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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