Hydrochloric Acid → HCID 19008983, compound

HRID 1742216Notes

Reaction equation

HRID 1742216 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH:18]2C(=O)NC(=O)NC2=O)=[CH:12][CH:11]=1.[OH-].[Na+].Cl>O>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 818524-Chloropyridine hydrochlorideHCID 190089865-[2-(4-Chlorophenyl)ethyl]-2,4,6(1H,3H,5H)-pyrimidinetrione

Product 1

HCID 19008983HCID 19008983, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
200 °C

Procedure

A mixture of 3 g (0.02 m) of 4-chloropyridine hydrochloride and 5.3 g (0.02 m) of 5-[2-(4-chlorophenyl)-ethyl]barbituric acid was thoroughly mixed with a mortar and pestle, heated in a 200° C. oil bath for 15-20 minutes, and then cooled. To the resulting product was added 5 g of NaOH and 40 mL of water, and the mixture was refluxed for several hours. After cooling the mixture, it was acidified with concentrated HCl, again refluxed for 45 minutes, and then cooled. The resulting material was diluted into water; the pH of the aqueous solution was adjusted to 7-8 with dilute NaOH; then the product was extracted into CH2Cl2. The CH2Cl2 layer was separated, filtered through phase separating paper, and concentrated. The residue was adsorbed onto silica gel and chromatographed using 5% EtOAc/CH2Cl2 >10% EtOAc/CH2Cl2 >5% MeOH/EtOAc (wash). Yield 0.82 g.

Workup

  1. additionwas thoroughly mixed with a mortar and pestle
  2. temperaturecooled
  3. temperaturethe mixture was refluxed for several hours
  4. temperatureAfter cooling the mixture, it
  5. temperatureagain refluxed for 45 minutes
  6. temperaturecooled
  7. extractionthen the product was extracted into CH2Cl2
  8. customThe CH2Cl2 layer was separated
  9. filtrationfiltered through phase
  10. customseparating paper
  11. concentrationconcentrated
  12. customchromatographed

Sources & evidence

ORD record
ord-f37793c340a24ff18d3df026e17947e7
Source dataset
uspto-grants-1994_08
Patent number
US05338742

Reaction notes

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