Formamide → N-cyano-N'-[2-(3-formylamino-2-oxobutylthio)ethyl]-N"-methylguanidine

HRID 477283Notes

Reaction equation

HRID 477283 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].[NH4+].C([O-])([O-])OC.O.O.O.O.P([O-])([O-])(O)=O.[NH4+].[Na+].[CH:37]([NH2:39])=[O:38].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:12]([NH:11][C:8]([NH:7][CH2:6][CH2:5][S:4][CH2:3][C:2](=[O:18])[CH:14]([NH:39][CH:37]=[O:38])[CH3:15])=[N:9][CH3:10])#[N:13]

Participants

8

Reactant 6

HCID 713FormamideHCID 516892Sodium BicarbonateHCID 2723923Ammonium formateHCID 14153741N-[2-(2-chloro-3-oxobutylthio)ethyl]-N'-cyano-N"-methylguanidineHCID 53629101MethylorthoformateHCID 56924540Ammonium sodium phosphate tetrahydrate

Product 1

HCID 14457222N-cyano-N'-[2-(3-formylamino-2-oxobutylthio)ethyl]-N"-methylguanidineYield 21%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 131 mg of N-[2-(2-chloro-3-oxobutylthio)ethyl]-N'-cyano-N"-methylguanidine, 320 mg of ammonium formate, 0.6 ml of methyl orthoformate and 209 mg of sodium ammonium hydrogenphosphate tetrahydrate were added 2.5 ml of formamide and 2.5 ml of chloroform, and the mixture was refluxed for 2 hours. Then, 420 mg of sodium hydrogencarbonate was added to the mixture and the solvent was removed under reduced pressure, and the obtained residue was refined by silica gel column chromatography (developing solvent: ethyl acetate/methanol=10/1) to obtain 28 mg of a colorless oily product (the yield was 21%).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6cbe34cb52e84d88a1fca85832fe3e02
Source dataset
uspto-grants-1989_12
Patent number
US04886910

Reaction notes

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