Sodium Bicarbonate → 4-Ethyl-5-(pyridin-2-yl)-1,3-oxazol-2(3H)-one

HRID 975850Notes

Reaction equation

HRID 975850 reaction equation
[O-:1][C:2]#[N:3].[K+].O[CH:6]([CH2:15][CH3:16])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8].C(=O)(O)[O-].[Na+]>Cl.O>[CH2:15]([C:6]1[NH:3][C:2](=[O:1])[O:8][C:7]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH3:16]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 11378442Potassium cyanateHCID 156704892-Hydroxy-1-(pyridin-2-yl)butan-1-one

Product 1

HCID 156704904-Ethyl-5-(pyridin-2-yl)-1,3-oxazol-2(3H)-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

Potassium cyanate (35.4 g, 0.44 mol) was added to a solution of 2-hydroxy-1-(2-pyridyl)butan-1-one (31 g, 0.15 mol) in 250 ml of 2N HCl diluted with 300 ml of water. After 1 hour the acidity was adjusted (pH=1) with concentrated hydrochloric acid and then allowed to stir overnight. The mixture was made basic by addition of aqueous sodium bicarbonate. The resulting gummy precipitate was chromatographed on silica gel and recrystallized twice from 50% aqueous ethanol to give the title compound, m.p. 196°-197° C. (dec.).

Workup

  1. customThe resulting gummy precipitate was chromatographed on silica gel
  2. customrecrystallized twice from 50% aqueous ethanol

Sources & evidence

ORD record
ord-ac3a73fcd3004e69970b22306e051db1
Source dataset
uspto-grants-1997_03
Patent number
US05610171

Reaction notes

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