Methyl isothiocyanate → N-Methyl-N'-(2-{[(pyridin-4-yl)methyl]amino}ethyl)thiourea
Reaction equation
[CH3:1][N:2]=[C:3]=[S:4].[N:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][CH2:13][CH2:14][NH2:15])=[CH:7][CH:6]=1>C(O)C>[CH3:1][NH:2][C:3]([NH:15][CH2:14][CH2:13][NH:12][CH2:11][C:8]1[CH:7]=[CH:6][N:5]=[CH:10][CH:9]=1)=[S:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methylisothiocyanate (1.46 g.) was added slowly to a solution of N-(4-picolyl)ethylenediamine (3.3 g.) in ethanol (25 ml.) The mixture was heated under reflux for 0.5 hours concentrated and extracted with isopropyl acetate to remove N-4-picolyl-N,N'-dimethylethane-1,2-bis thiourea (m.p. 173°-4°). The mother liquors were concentrated and the residue purified by column chromatography to afford the title compound.
Workup
- temperaturewas heated
- temperatureunder reflux for 0.5 hours
- concentrationconcentrated
- extractionextracted with isopropyl acetate
- customto remove N-4-picolyl-N,N'-dimethylethane-1,2-bis thiourea (m.p. 173°-4°)
- concentrationThe mother liquors were concentrated
- customthe residue purified by column chromatography
Sources & evidence
- ORD record
- ord-482ae297863a49f4939c559e2d644977
- Source dataset
- uspto-grants-1977_04
- Patent number
- US04018928
Reaction notes
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