Hydrochloric Acid → N-methyl-N'-[2-(3-methoxy-2-pyridylmethylthio)ethyl]guanidine

HRID 263263Notes

Reaction equation

HRID 263263 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][N:7]=1.CN.[C:16]([NH:24][C:25](N)=[NH:26])(=O)C1C=CC=CC=1.Cl>C(O)C>[CH3:16][NH:24][C:25]([NH:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][N:7]=1)=[NH:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 129515352-{[(3-Methoxypyridin-2-yl)methyl]sulfanyl}ethan-1-amineHCID 178513056N-carbamimidoylbenzamide

Product 1

HCID 178485114N-methyl-N'-[2-(3-methoxy-2-pyridylmethylthio)ethyl]guanidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of 2-[2-aminoethylthiomethyl]-3-methoxypyridine in ethanol is added to a stirred solution of N-benzoyl dimethyldithioimidocarbonate in ethanol and the mixture is stirred overnight at room temperature. The purified product is treated with methylamine in ethanol and the resultant benzoylguanidine is hydrolysed by refluxing with aqueous hydrochloric acid to give N-methyl-N'-[2-(3-methoxy-2-pyridylmethylthio)ethyl]guanidine.

Sources & evidence

ORD record
ord-35171ba44e054624a07473fb253992a9
Source dataset
uspto-grants-1979_05
Patent number
US04156727

Reaction notes

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