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

HRID 973417Notes

Reaction equation

HRID 973417 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 silca 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 silca gel
  2. customrecrystallized twice from 50% aqueous ethanol

Sources & evidence

ORD record
ord-849e9e2ccaa04aa29884682a71271759
Source dataset
uspto-grants-1991_11
Patent number
US05063238

Reaction notes

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