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

HRID 2083068Notes

Reaction equation

HRID 2083068 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-355df910dab042909520b0651d68c951
Source dataset
uspto-grants-1978_04
Patent number
US04083983

Reaction notes

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