Hydrochloric Acid → 4-Ethyl-5-pyridin-4-yl-2(3H)thiazolone

HRID 652057

Reaction equation

HRID 652057 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7](Br)[C:8](=O)[CH2:9][CH3:10])=[CH:3][CH:2]=1.C([NH:16][C:17](N)=[S:18])(=O)C.[O-:20]C#N.[K+].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:9]([C:8]1[NH:16][C:17](=[O:20])[S:18][C:7]=1[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)[CH3:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723593AcetylthioureaHCID 11378442Potassium cyanateHCID 201992181-(4-Pyridyl)-1-bromo-2-butanone

Product 1

HCID 201450164-Ethyl-5-pyridin-4-yl-2(3H)thiazolone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1-(4-Pyridyl)-1-bromo-2-butanone (28.8 g, 0.1 mol) and 1-acetyl-2-thiourea (13.0 g, 0.11 mol) are combined in 200 ml absolute ethanol and refluxed 24 hours. The solvent is evaporated and the residue is purified by chromatography. The thiol is mixed with (8.1 g, 0.1 mol) potassium cyanate and 0.2 mol 10% aqueous hydrochloric acid. The mixture is heated to 80° C. for 15 minutes, then cooled. The acid is adjusted to ph=6.5 with solid sodium bicarbonate which causes the product to precipitate.

Workup

  1. temperaturerefluxed 24 hours
  2. customThe solvent is evaporated
  3. customthe residue is purified by chromatography
  4. temperaturecooled
  5. customto precipitate

Sources & evidence

ORD record
ord-59335595239343ebbaf7e4fe817cfef8
Source dataset
uspto-grants-1987_06
Patent number
US04670450

Linked notes

Loading…