Hydrochloric Acid → ethyl 6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
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
Procedure
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.
Workup
- customThe resulting reaction mixture
- temperaturewas heated
- temperatureat reflux for 6 hours
- customtriturated
- customA small amount of a white solid precipitated out
- temperatureto cool in the refrigerator overnight
- customThe precipitate formed
- filtrationwas filtered off
- washwashed with more absolute ethanol
Sources & evidence
- ORD record
- ord-ddac34ba67dc4153b879d5299f7ceb16
- Source dataset
- uspto-grants-1988_06
- Patent number
- US04753946
Reaction notes
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