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

HRID 1856267Notes

Reaction equation

HRID 1856267 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-cf8e4233496841348b521a351fcac1ef
Source dataset
uspto-grants-1980_08
Patent number
US04218452

Reaction notes

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