Thiourea → HCID 22170065, compound

HRID 1822783Notes

Reaction equation

HRID 1822783 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5](=O)[CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[NH2:16][C:17]([NH2:19])=[S:18].[O-]CC.[Na+]>C(O)C>[CH:8]1([O:7][CH2:6][C:5]2[NH:19][C:17](=[S:18])[NH:16][C:3](=[O:2])[CH:4]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 2723922Sodium ethoxideHCID 23568707HCID 23568707, compound

Product 1

HCID 22170065HCID 22170065, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Cyclohexyloxy-3-oxo-butyric acid methyl ester (8.0 g) was added to a mixture of thiourea (34.7 g), sodium ethoxide (180 mL of 3 M ethanol solution) and ethanol (70 mL). The reaction was heated at reflux under nitrogen for 16 h. The ethanol was removed under vacuum. Residue was dissolved in water (400 mL) and the solution was cooled in an ice-bath. The solution was acidified with conc. hydrochloric acid to pH˜1 and stood at rt for 16 h. The solid that formed was collected by filtration to afford 6-cyclohexyloxymethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (7.6 g).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux under nitrogen for 16 h
  3. customThe ethanol was removed under vacuum
  4. dissolutionResidue was dissolved in water (400 mL)
  5. temperaturethe solution was cooled in an ice-bath
  6. customThe solid that formed
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-11a9226f185b482e9e1af1c46c7814fd
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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