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

HRID 1590281노트

반응식

HRID 1590281 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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-pyrimidine-carboxylic acid, ethyl ester; m.p. 208°-209°. TLC (silica gel; ethyl acetate:hexanes, 1:1) Rf =0.45.

후처리

  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

출처 및 근거

ORD 기록
ord-2bd21664b3f94a8286f49f6770ea9e16
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05202330

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