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

HRID 262483
Notes
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Reaction equation

HRID 262483 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]
ParticipantsProcedureSources & evidenceReaction notes

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 702
Ethanol
Solvent
3×

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-0cd46469629f4f3d9c659c7129568bb7
Source dataset
uspto-grants-1979_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04154838

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes