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

HRID 568336Notes

Reaction equation

HRID 568336 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-07ff22705d43415281ec8fdd63ae4899
Source dataset
uspto-grants-1988_03
Patent number
US04728652

Reaction notes

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