1,1-Bis(methylthio)-2-nitroethylene → 2-Nitromethylene-1-(6-chloro-3-pyridyl)-6methylhexahydropyrimidine
Reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([NH:6][C:7]1[CH:8]=[N:9][C:10]([Cl:13])=[CH:11][CH:12]=1)[CH3:5].CS[C:16](SC)=[CH:17][N+:18]([O-:20])=[O:19]>C(O)C>[N+:18]([CH:17]=[C:16]1[NH:1][CH2:2][CH2:3][CH:4]([CH3:5])[N:6]1[C:7]1[CH:8]=[N:9][C:10]([Cl:13])=[CH:11][CH:12]=1)([O-:20])=[O:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A mixture of 1-amino-3-[N-(6-chloro-3-pyridyl)amino]butane (0.94 g, 0.0047 mol) (ex Example 6), 1,1-bis(methylthio)-2-nitroethene (0.78 g, 0.0047 mol) and ethanol (100 ml) was heated under reflux for 24 hours. The resulting mixture was cooled to ambient temperature (20° C.) and filtered to isolate the product 2-nitromethylene-1-(6-chloro-3-pyridyl)-6methylhexahydropyrimidine as a white solid in a yield of 0.3 g (25%), m.p. 184.5° C.
Workup
- temperaturewas heated
- temperatureunder reflux for 24 hours
- filtrationfiltered
Sources & evidence
- ORD record
- ord-be4fbf72bcfc417e845d6cee35546451
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05039686
Reaction notes
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