Hydrochloric Acid → HCID 178518203, compound

HRID 980155Notes

Reaction equation

HRID 980155 reaction equation
[OH-].[NH4+].[OH:3][C:4]1[NH:9][C:8](=S)[NH:7][C:6](=[O:11])[C:5]=1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13].N1C=CC=NC=1.Cl>[Ni].O>[OH:3][CH:4]1[CH:5]([C:12]([NH:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:13])[C:6](=[O:11])[N:7]=[CH:8][NH:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9260PyrimidineHCID 14923Ammonium HydroxideHCID 300067197534-21-9

Product 1

HCID 178518203HCID 178518203, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent2×

Procedure

To concentrated aqueous ammonium hydroxide (400 ml) and water (400 ml) was added 1,2,3,4-tetrahydro-6-hydroxy-4-oxo-N-phenyl-2-thioxo-5-pyrimidinecarboxamide (13.2 g) (prepared as described in Example 1 of the aforesaid copending application Ser. No. 699,776). The pyrimidine dissolved. To this solution was added a slurry of Raney Nickel in water (50 g). The suspension was gently refluxed with stirring for four hours. It was cooled and the solids, which consisted of product and inorganics, were treated with dilute hydrochloric acid, the mixture filtered and the solids extracted with 2-Normal sodium hydroxide solution and filtered. The filtrate was then acidified with dilute hydrochloric acid, the resulting precipitate redissolved in aqueous ammonium hydroxide, purified with activated charcoal and celite, and reprecipitated with dilute acid. The solid was collected, washed with water and dried. Yield 5.8 g, melting point 200°-208°. Mass spectrum 231, calculated 231; Nuclear Magnetic Resonance (DMSO), 6.8-7.7 δ (aromatic peaks); 8.28 δ (2-hydrogen atom); 11.8 δ (exchangeable protons).

Workup

  1. customprepared
  2. temperatureThe suspension was gently refluxed
  3. temperatureIt was cooled
  4. filtrationthe mixture filtered
  5. extractionthe solids extracted with 2-Normal sodium hydroxide solution
  6. filtrationfiltered
  7. dissolutionthe resulting precipitate redissolved in aqueous ammonium hydroxide
  8. custompurified with activated charcoal and celite
  9. customreprecipitated
  10. additionwith dilute acid
  11. customThe solid was collected
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-00a11e1ab58e4d4c9da0e43c8ef6d6d2
Source dataset
uspto-grants-1987_01
Patent number
US04636508

Reaction notes

Loading…