Acetonitrile → HCID 70513664, compound
Reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:9][C:8]([CH2:10][S:11][CH2:12][CH2:13]N)=[CH:7][CH:6]=1)[CH3:3].[CH:15]1([NH:23][C:24](SC)=[CH:25][N+:26]([O-:28])=[O:27])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(#[N:33])C>>[CH3:3][N:2]([CH2:4][C:5]1[S:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][N:23]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[C:24]([NH2:33])=[CH:25][N+:26]([O-:28])=[O:27])=[CH:7][CH:6]=1)[CH3:1]Participants
4
Procedure
A solution of 2-[[[5-(dimethylamino)methyl-2-thienyl]methyl]thio]ethanamine (1.00 g) and 1-cyclooctylamino-1-methylthio-2-nitroethene (1.17 g) in acetonitrile (4 ml) was heated at reflux temperature for 8 days. The solvent was then evaporated in vacuo and the residue partitioned between water (25 ml) and ethyl acetate (25 ml). The aqueous phase was then extracted with ethyl acetate (2×25 ml) and the combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by column chromatography on alumina using pentane/chloroform mixtures as eluant to give N-[2-[[5-(dimethylamino)methyl-2-thienyl]methyl]thioethyl]-N-cyclooctyl-2-nitro-1,1-ethenediamine (0.62 g) as an orange oil.
Workup
- temperatureat reflux temperature for 8 days
- customThe solvent was then evaporated in vacuo
- customthe residue partitioned between water (25 ml) and ethyl acetate (25 ml)
- extractionThe aqueous phase was then extracted with ethyl acetate (2×25 ml)
- dry with materialthe combined organic extracts were dried (Na2SO4)
- customevaporated in vacuo
- customThe residue was purified by column chromatography on alumina
Sources & evidence
- ORD record
- ord-3a5c2f272c864c88b2a37981baee3f5d
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04427685
Reaction notes
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