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

HRID 1588480ノート

反応式

HRID 1588480 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
140 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-45c7ca5e7ed24446a4304ccee2310eb7
出典データセット
uspto-grants-1993_06
特許番号
US05223505

反応ノート

読み込み中…