Ethyl isocyanate → 4-[[(Dimethylamino)methylene]amino]-3-pyridinol ethylcarbamate

HRID 361332

Reaction equation

HRID 361332 reaction equation
[CH3:1][N:2]([CH:4]=[N:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[OH:12])[CH3:3].[H-].[Na+].[CH2:15]([N:17]=[C:18]=[O:19])[CH3:16]>O1CCCC1>[CH2:15]([NH:17][C:18]([O:12][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:6]=1[N:5]=[CH:4][N:2]([CH3:1])[CH3:3])=[O:19])[CH3:16]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 24758Sodium hydrideHCID 153809294-[[(Dimethylamino)methylene]amino]-3-pyridinol

Product 1

HCID 677490814-[[(Dimethylamino)methylene]amino]-3-pyridinol ethylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a warm solution of 4-[[(dimethylamino)methylene]amino]-3-pyridinol (7.12 g) in dry tetrahydrofuran (150 mL) were added sodium hydride (173 mg) and ethyl isocyanate (3.59 mL). The reaction mixture was stirred at room temperature overnight, cooled in an ice bath and filtered, and the solid was washed with diethyl ether. The solid was distributed between methylene chloride (250 mL) and saturated ammonium chloride (30 mL) and extracted twice more with methylene chloride (100 mL). The solution was dried (MgSO4) and concentrated, and the solid was recrystallized from ethyl acetate to yield 5.7 g of needles, m.p. 138° C. (dec.).

Workup

  1. temperaturecooled in an ice bath
  2. filtrationfiltered
  3. washthe solid was washed with diethyl ether
  4. extractionextracted twice more with methylene chloride (100 mL)
  5. dry with materialThe solution was dried (MgSO4)
  6. concentrationconcentrated
  7. customthe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-eebf09d61fdd47db921fe997da173ffc
Source dataset
uspto-grants-1999_02
Patent number
US05866565

Linked notes

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