Hydrochloric Acid → HCID 178515858, compound

HRID 1729238Notes

Reaction equation

HRID 1729238 reaction equation
[Na].[C:2]1([CH2:8][C:9](=O)[CH2:10][C:11]([O:13]CC)=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]([NH2:20])=[S:19].Cl>C(O)C.O>[OH:13][C:11]1[CH:10]=[C:9]([CH2:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:20]=[C:18]([SH:19])[N:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 225855Ethyl 3-oxo-4-phenylbutanoateHCID 2723790ThioureaHCID 5360545Sodium

Product 1

HCID 178515858HCID 178515858, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium (11.5 g, 0.5 mol) was dissolved in ethanol (700 ml) and ethyl 4-phenylacetoacetate added with mechanical stirring. Further ethanol (350 ml) and thiourea (22.8 g, 0.3 mol) were added and the reaction mixture heated under reflux for 24 hours. The reaction mixture was then cooled, poured into water (2 liters) and acidified with concentrated hydrochloric acid to approximately pH5. The resulting precipitate was filtered off, washed with water (3×500 ml) and diethyl ether (2×300 ml) and dried under vacuum to afford 41.5 g 4-hydroxy-6-phenylmethyl-2-mercaptopyrimidine as a beige solid, m.pt., 215°-220° C. with decomposition. M+ found: 218.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 24 hours
  3. temperatureThe reaction mixture was then cooled
  4. filtrationThe resulting precipitate was filtered off
  5. washwashed with water (3×500 ml) and diethyl ether (2×300 ml)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-95e4254ea7d549c49872e6bb02047b8c
Source dataset
uspto-grants-1994_07
Patent number
US05332745

Reaction notes

Loading…