Thiourea → HCID 13505307, compound

HRID 224877Notes

Reaction equation

HRID 224877 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[CH:5]([CH:7]([CH:13]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH3:14])[C:8](OCC)=O)=[O:6].[O-]CC.[Na+]>C(O)C>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH:13]([C:7]2[C:5](=[O:6])[NH:1][C:2](=[S:3])[NH:4][CH:8]=2)[CH3:14])[CH:16]=1

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 2723922Sodium ethoxideHCID 20213316Ethyl 2-formyl-3-(3-pyridyl)butyrate

Product 1

HCID 13505307HCID 13505307, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiourea (1.4 g) and ethyl 2-formyl-3-(3-pyridyl)butyrate (3.4 g) was added to a solution of sodium ethoxide (from 0.78 g sodium) in ethanol (45 ml). The mixture was heated under reflux for 7 hours and evaporated. The residue was taken up in water and extracted with chloroform at pH 13. The pH was adjusted to 7.0 and the mixture allowed to stand at 0° overnight. The solid was filtered off to give 5-[1-(3-pyridyl)ethyl]2-thiouracil (1.83 g) m.p. 225°-228° (from 2-propanol).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 7 hours
  3. customevaporated
  4. extractionextracted with chloroform at pH 13
  5. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-ff65173244274c8aa95bb3031c05511c
Source dataset
uspto-grants-1980_11
Patent number
US04234588

Reaction notes

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