Methanol → HCID 178475104, compound
Reaction equation
S(O)(O)(=O)=O.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][NH:13][C:14]([NH2:16])=[NH:15].[CH3:17][O-:18].[Na+].[CH3:20]O>C(O)C>[C:17]([NH:15][C:14]([NH:13][CH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][N:6]=1)=[NH:16])(=[O:18])[CH3:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
19.92 g of 1-(2-pyridylmethyl) guanidine sulfate and 5.94 g of sodium methoxide are added to 100 ml of methanol. The mixture is stirred for 21/2 hrs. at RT and filtered. The resulting solid is washed with methanol, and the solvent evaporated in vacuo, yielding a red solid. Absolute ethanol is added to the red solid in two stages and the resulting mixture is filtered. The filtered solid is washed with absolute ethanol and the solvent evaporated in vacuo yielding the guanidine as a solid. The guanidine is dissolved in 150 ml of boiling ethyl acetate and the solution separated from any residue and concentrated under N2. The concentrated solution is heated in a sealed stainless steel bomb at 100° C. for one day. The reaction mixture is cooled, diluted with ethyl acetate containing a trace of methanol, heated, concentrated and cooled, resulting in the formation of a precipitate. The precipitate is washed with ethyl acetate and dried in vacuo yielding the desired acetyl guanidine as a white powder, M.P. 148°-150° C.
Workup
- filtrationat RT and filtered
- washThe resulting solid is washed with methanol
- customthe solvent evaporated in vacuo
- customyielding a red solid
- filtrationthe resulting mixture is filtered
- washThe filtered solid is washed with absolute ethanol
- customthe solvent evaporated in vacuo
Sources & evidence
- ORD record
- ord-be94d867c4c54cf6beef5e8df56119c7
- Source dataset
- uspto-grants-1985_01
- Patent number
- US04496573
Reaction notes
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