Hydrochloric Acid → HCID 19008990, compound

HRID 1742217Notes

Reaction equation

HRID 1742217 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH:12]2[C:17](=O)NC(=O)NC2=O)=[CH:6][CH:5]=1)[CH3:2].Cl.ClC1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.[OH-].[Na+].Cl>O>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:17]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 818524-Chloropyridine hydrochlorideHCID 19008987HCID 19008987, compound

Product 1

HCID 19008990HCID 19008990, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.5 g (0.0235 m) of 5-[2-(4-ethoxyphenyl)ethyl]barbituric acid and 7 g (0.047 m) of 4-chloropyridine hydrochloride was mixed with a mortar and pestle and heated in an oil bath until the reagents formed a melt (185° C.). The mixture was kept at 180°-185° for 15-20 minutes, when the mixture began to noticeably darken. When heat was removed, the mixture quickly formed a hard glass. To this product, 6.5 g of NaOH pellets and 40 mL of water was added, and the mixture was refluxed for 5-6 hours. After cooling, the mixture was acidified with concentrated HCl and refluxed for 11/2 hours. The mixture was then diluted over ice, and the pH was adjusted to neutral using dilute NaOH. The product was then extracted into CH2Cl2. The CH2Cl2 layer was separated, dried, adsorbed onto silica gel, and chromatographed using CH2Cl2 >50% EtOAc/CH2Cl2. The product was an oil which crystallized. Yield 0.5 g. MP 79°-81° C.

Workup

  1. additionwas mixed with a mortar and pestle
  2. temperatureheated in an oil bath until the reagents
  3. customformed a melt (185° C.)
  4. temperatureWhen heat
  5. customwas removed
  6. customthe mixture quickly formed a hard glass
  7. temperaturethe mixture was refluxed for 5-6 hours
  8. temperatureAfter cooling
  9. temperaturerefluxed for 11/2 hours
  10. additionThe mixture was then diluted over ice
  11. extractionThe product was then extracted into CH2Cl2
  12. customThe CH2Cl2 layer was separated
  13. customdried
  14. customchromatographed
  15. customcrystallized

Sources & evidence

ORD record
ord-aabcc05e10854c48869a1c0e12f8406d
Source dataset
uspto-grants-1994_08
Patent number
US05338742

Reaction notes

Loading…