Ethyl 3-oxo-2-(2-phenylethyl)butanoate → 5-(2-Phenylethyl)-6-methyl-2-thiouracil

HRID 237064

Reaction equation

HRID 237064 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]([C:15]([CH3:17])=O)[C:10](OCC)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:18][C:19]([NH2:21])=[S:20].[O-]CC.[Na+].[Na]>C(O)C>[C:1]1([CH2:7][CH2:8][C:9]2[C:10](=[O:11])[NH:18][C:19](=[S:20])[NH:21][C:15]=2[CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 219459Ethyl 3-oxo-2-(2-phenylethyl)butanoateHCID 2723790ThioureaHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 129459705-(2-Phenylethyl)-6-methyl-2-thiouracil

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl α-(phenylethyl)acetoacetate (23.4 g) and thiourea (10.65 g) were added to a solution of sodium ethoxide in ethanol (100 ml) prepared from sodium (4.6 g). The mixture was refluxed for 51/2 hours and evaporated to dryness. The solid residue was dissolved in water and acetic acid was added to pH 4. The white precipitate was filtered off and recrystallised from ethanol to give 5-(2-phenylethyl)-6-methyl-2-thiouracil m.p. 210°-214°.

Workup

  1. temperatureThe mixture was refluxed for 51/2 hours
  2. customevaporated to dryness
  3. dissolutionThe solid residue was dissolved in water
  4. additionacetic acid was added to pH 4
  5. filtrationThe white precipitate was filtered off
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-4af3bbe7023a4bd1bc4c638c8bdf57ba
Source dataset
uspto-grants-1979_06
Patent number
US04159329

Linked notes

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