Hydrochloric Acid → HCID 18752905, compound

HRID 1838083Notes

Reaction equation

HRID 1838083 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH2:18]Cl)[C:14]([NH2:17])=[N:15][CH:16]=1.Cl>C1COCC1>[Cl:10][C:11]1[CH:12]=[C:13]([CH2:18][O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:14]([NH2:17])=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 24758Sodium hydrideHCID 18752881HCID 18752881, compound

Product 1

HCID 18752905HCID 18752905, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydride (80% in oil, 124 mg, 4.1 mmol) was added portionwise to a solution of phenol (290 mg, 3.1 mmol) in anhydrous THF (15 ml). 5-Chloro-3-(chloromethyl)-2-pyridinamine.HCl (R. Herbert, D. G. Wibberley, J. Chem. Soc., 1969, 1504) (300 mg, 1.4 mmol) was then added and the reaction stirred at 50° C. for 3 h. After removal of THF in vacuo, the residue was partioned between diethyl ether and 1N NaOH. The aqueous phase was removed, extracted with diethyl ether and the combined organics washed with saturated brine, dried over MgSO4 and concentrated to an oil which upon triturating with hexane gave the title compound as a white solid (265 mg, 1.1 mmol):

Workup

  1. customAfter removal of THF in vacuo
  2. customThe aqueous phase was removed
  3. extractionextracted with diethyl ether
  4. washthe combined organics washed with saturated brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to an oil which
  7. customupon triturating with hexane

Sources & evidence

ORD record
ord-38758e861a614c25aaff61bca0465e6a
Source dataset
uspto-grants-2004_01
Patent number
US06673789B2

Reaction notes

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