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

HRID 568336ノート

反応式

HRID 568336 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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution containing m-nitrobenzaldehyde (7.55 g., 50.0 mmole), ethylacetoacetate (6.5 g., 50.0 mmole), and thiourea (3.8 g., 50.0 mmole) in absolute ethanol (30 ml.) is treated with concentrated hydrochloric acid (0.2 ml.). The resulting reaction mixture is heated at reflux for 6 hours. It is then cooled to room temperature and triturated. A small amount of a white solid precipitates out. The reaction flask is then allowed to cool in the refrigerator overnight. The precipitate that forms is filtered off and washed with additional absolute ethanol to provide 2.5 g. of colorless solid product. Recrystallization from absolute ethanol gives an analytically pure sample of 1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-thioxo-5-pyrimidinecarboxylic acid, ethyl ester; m.p. 208°-209°. TLC (silica gel; ethyl acetate:hexane, 1:1) Rf =0.45.

後処理

  1. customThe resulting reaction mixture
  2. temperatureis heated
  3. temperatureat reflux for 6 hours
  4. customtriturated
  5. customA small amount of a white solid precipitates out
  6. temperatureto cool in the refrigerator overnight
  7. filtrationThe precipitate that forms is filtered off
  8. washwashed with additional absolute ethanol
  9. customto provide 2.5 g
  10. customRecrystallization from absolute ethanol

出典と根拠

ORDレコード
ord-07ff22705d43415281ec8fdd63ae4899
出典データセット
uspto-grants-1988_03
特許番号
US04728652

反応ノート

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