Formamide → N-cyano-N'-[2-(3-formylamino-2-oxobutylthio)ethyl]-N"-methylguanidine
Reaction equation
Cl[CH:2]([C:14](=O)[CH3:15])[CH2:3][S:4][CH2:5][CH2:6][NH:7][C:8]([NH:11][C:12]#[N:13])=[N:9][CH3:10].C([O-])=[O:18].[Na+].C([O-])=O.[NH4+].C(=O)([O-])O.[Na+].[CH:30]([NH2:32])=[O:31]>>[C:12]([NH:11][C:8]([NH:7][CH2:6][CH2:5][S:4][CH2:3][C:2](=[O:18])[CH:14]([NH:32][CH:30]=[O:31])[CH3:15])=[N:9][CH3:10])#[N:13]Participants
6
Procedure
In 2.5 ml of formamide were dissolved 131 mg of N-[2-(2-chloro-3-oxobutylthio)ethyl]-N'-cyano-N"-methylguanidine, 136 mg of sodium formate and 320 mg of ammonium formate, and the solution was stirred at room temperature for 3 days. Then, 420 mg of sodium hydrogencarbonate was added to the solution and formamide was removed under reduced pressure, and the obtained residue was refined by silica gel column chromatography (developing solvent: chloroform/ethanol=5/1) to obtain 28 mg of a colorless oily product (the yield was 19%).
Workup
- customwas removed under reduced pressure
Sources & evidence
- ORD record
- ord-bef66331277f4ed6b63d2b7c21f53649
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04886910
Reaction notes
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