Hydrochloric Acid → Methyl 3-(4-dimethylaminomethyl-2-pyridylmethylthio)propionimidate
Reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][C:15]#[N:16])[CH:6]=1)[CH3:3].Cl.[C:18](=O)([O-])[O-:19].[K+].[K+]>CO.C(Cl)(Cl)Cl>[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][C:15](=[NH:16])[O:19][CH3:18])[CH:6]=1)[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -5 °C
Procedure
3-(4-Dimethylaminomethyl-2-pyridylmethylthio)propionitrile (13.60 g) was dissolved in a mixture of dry methanol (70 ml) and dry chloroform (140 ml) and the stirred solution cooled to -5° C. under nitrogen. Dry hydrogen chloride gas was passed through the solution for 3.75 hours, keeping the temperature below 0° C. The solution was allowed to stand in a stoppered flask at ca. 4° C. for 24 hours and was added to a solution of potassium carbonate (45 g) in ice-water (500 ml). The chloroform layer was separated off and the aqueous layer extracted with chloroform (3×150 ml). The combined extracts were dried (K2CO3 and chloroform evaporated at reduced pressure to give methyl 3-(4-dimethylaminomethyl-2-pyridylmethylthio)propionimidate (14.02 g) as an oil.
Workup
- customthe temperature below 0° C
- customThe chloroform layer was separated off
- extractionthe aqueous layer extracted with chloroform (3×150 ml)
- dry with materialThe combined extracts were dried (K2CO3 and chloroform
- customevaporated at reduced pressure
Sources & evidence
- ORD record
- ord-6af52600af014c9684fa2c1281cc5ab6
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04808589
Reaction notes
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