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

HRID 1588480

반응식

HRID 1588480 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
140 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-45c7ca5e7ed24446a4304ccee2310eb7
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05223505

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