Hydrochloric Acid → {4-[2-(2-Methoxy-phenyl)-ethyl]-pyridin-2-yl}-urea

HRID 1023450Notes

Reaction equation

HRID 1023450 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([NH:15][C:16]([NH:18][C:19]1[CH:24]=[C:23]([CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH:22]=[CH:21][N:20]=1)=[O:17])(=O)C1C=CC=CC=1.Cl>C(O)C>[CH3:34][O:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][CH2:25][C:23]1[CH:22]=[CH:21][N:20]=[C:19]([NH:18][C:16]([NH2:15])=[O:17])[CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 690823961-Benzoyl-3-{4-[2-(2-methoxy-phenyl)-ethyl]-pyridin-2-yl}-urea

Product 1

HCID 69082641{4-[2-(2-Methoxy-phenyl)-ethyl]-pyridin-2-yl}-urea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Potassium carbonate (93.2 mg, 0.674 mmol) is added to a solution of the crude 1-benzoyl-3-{4-[2-(2-methoxy-phenyl)-ethyl]-pyridin-2-yl}-urea (211 mg) in absolute ethanol (3 mL), and the mixture is heated at 85° C. After 2 hours, the mixture is cooled to room temperature, neutralized with 1 M aqueous HCl to pH 7-8, and stirred over night. The mixture is filtered, and the solids are washed with EtOH (2×0.5 mL) and air dried. The solids are partitioned between ethyl acetate (10 mL) and saturated aqueous NaHCO3 (3 mL). The organic layer is dried over MgSO4, filtered and concentrated to give the titled product.

Workup

  1. temperaturethe mixture is cooled to room temperature
  2. filtrationThe mixture is filtered
  3. washthe solids are washed with EtOH (2×0.5 mL) and air
  4. customdried
  5. customThe solids are partitioned between ethyl acetate (10 mL) and saturated aqueous NaHCO3 (3 mL)
  6. dry with materialThe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f2546606d5c84d1f83bd843961a0a03f
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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