Thiourea → HCID 18184197, compound

HRID 1358334Notes

Reaction equation

HRID 1358334 reaction equation
C[O-].[Na+].C[O:5][C:6](=O)[CH:7]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[C:8](OC)=[O:9].[NH2:22][C:23]([NH2:25])=[S:24]>CO>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][CH:7]1[C:6](=[O:5])[NH:25][C:23](=[S:24])[NH:22][C:8]1=[O:9]

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 10942334Sodium MethoxideHCID 12967085Dimethyl 2-(2-methoxyphenoxy)malonate

Product 1

HCID 18184197HCID 18184197, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

12.15 g sodium methylate was dissolved in 200 ml methanol and 21.1 g dimethyl-(o-methoxyphenoxy)malonate was added. Stirring was continued for 130 min. The mixture was cooled to 10° C. and 7.6 g thiourea was added. Stirring was continued for 24 h. The solvent was evaporated in vacuo. The residue was stirred with diethyl ether. The ether layer was filtered off and the solid was dissolved in 60 ml water and acidified to pH=4 with conc. acetic acid. The precipitated product was filtered and washed with methanol and dried at 30° C. and reduced pressure to give 19.8 g 5-(o-methoxyphenoxy)-2-thioxo-dihydro-pyrimidine-4,6-dione (or a tautomere thereof.

Workup

  1. stirringStirring
  2. waitwas continued for 24 h
  3. customThe solvent was evaporated in vacuo
  4. stirringThe residue was stirred with diethyl ether
  5. filtrationThe ether layer was filtered off
  6. dissolutionthe solid was dissolved in 60 ml water
  7. filtrationThe precipitated product was filtered
  8. washwashed with methanol
  9. customdried at 30° C.

Sources & evidence

ORD record
ord-8746717e62b14e838bb5eb154403bfc9
Source dataset
uspto-grants-2003_07
Patent number
US06596719B1

Reaction notes

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