Hydrochloric Acid → ethyl 6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 580501ノート

反応式

HRID 580501 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[CH2:12]([O:14][C:15](=[O:20])[CH2:16][C:17]([CH3:19])=O)[CH3:13].[NH2:21][C:22]([NH2:24])=[S:23].Cl>C(O)C>[CH3:19][C:17]1[NH:24][C:22](=[S:23])[NH:21][CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:16]=1[C:15]([O:14][CH2:12][CH3:13])=[O:20]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 74493-NitrobenzaldehydeHCID 8868Ethyl AcetoacetateHCID 2723790Thiourea

生成物 1

HCID 2787683ethyl 6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate収率 15.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

The solution containing m-nitrobenzaldehyde (7.55 g, 50.0 mmoles), ethyl-acetoacetate (6.5 g, 50.0 mmoles) and thiourea (3.8 g, 50.0 mmoles) in absolute ethanol (30 ml) was treated with concentrated hydrochloric acid (0.2 ml). The resulting reaction mixture was heated at reflux for 6 hours. It was then cooled to room temperature and triturated. A small amount of a white solid precipitated out. The reaction flask was then allowed to cool in the refrigerator overnight. The precipitate formed was filtered off and washed with more absolute ethanol to provide colorless solid (2.5 g). For analytical purposes, this material was recrystallized from absolute ethanol to give colorless crystals, m.p. 208°-209° C.

後処理

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 6 hours
  4. customtriturated
  5. customA small amount of a white solid precipitated out
  6. temperatureto cool in the refrigerator overnight
  7. customThe precipitate formed
  8. filtrationwas filtered off
  9. washwashed with more absolute ethanol

出典と根拠

ORDレコード
ord-ddac34ba67dc4153b879d5299f7ceb16
出典データセット
uspto-grants-1988_06
特許番号
US04753946

反応ノート

読み込み中…