4-Thioureidoanisole → 2,3-dihydro-1-(4-methoxyphenyl)-6-methyl-2-thioxo-4(1H)pyrimidinone

HRID 1588480

Reaction equation

HRID 1588480 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH2:12])=[S:11])=[CH:5][CH:4]=1.CC1[O:19][C:18](=O)[CH2:17][C:16](C)([CH3:21])O1.O1C=COCC1=O>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:16]([CH3:21])=[CH:17][C:18](=[O:19])[NH:12][C:10]2=[S:11])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6675494-ThioureidoanisoleHCID 153305632,6,6-Trimethyl-1,3-dioxin-4-oneHCID 54144957Dioxinone

Product 1

HCID 197542352,3-dihydro-1-(4-methoxyphenyl)-6-methyl-2-thioxo-4(1H)pyrimidinoneYield 72.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
140 °C

Procedure

N-(4-Methoxyphenyl)thiourea (18.2 g, 100 mM) and 2,6,6-trimethyl-1,3-dioxin-4-one (21.3 g, 150 mM) were heated together at 140° C. (bath temperature) for 30 minutes. The solid product was cooled, treated with ethanol (100 ml), boiled for 10 minutes, cooled and the solid product was isolated by filtration. More dioxinone (21.3 g) was added to the above material and the mixture was heated at 140° C. for a further 20 minutes. Ethanol (50 ml) was then added to the cooled mixture, which was then heated under reflux for 5 minutes. The mixture was cooled and the solid product isolated by filtration to give 2,3-dihydro-1-(4-methoxyphenyl)-6-methyl-2-thioxo-4(1H)pyrimidinone (17.9 g, 72% yield) m.p. 248°-249° C.; microanalysis, found: C,58.2; H,4.9; N,11.0%; C12H12N2OS requires: C,58.1; H,4.8; N,11.3%.

Workup

  1. temperatureThe solid product was cooled
  2. temperaturecooled
  3. customthe solid product was isolated by filtration
  4. temperaturewas then heated
  5. temperatureunder reflux for 5 minutes
  6. temperatureThe mixture was cooled
  7. customthe solid product isolated by filtration

Sources & evidence

ORD record
ord-45c7ca5e7ed24446a4304ccee2310eb7
Source dataset
uspto-grants-1993_06
Patent number
US05223505

Linked notes

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