Methylamine → HCID 53848828, compound

HRID 1974423Notes

Reaction equation

HRID 1974423 reaction equation
CS[C:3](=[N:6][C:7]#[N:8])SC.[NH2:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[C:19]([Br:20])=[CH:18][CH:17]=[CH:16][N:15]=1.[CH3:21][NH2:22]>C(O)C>[C:21]([NH:8][C:7]([NH:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[C:19]([Br:20])=[CH:18][CH:17]=[CH:16][N:15]=1)=[N:6][CH3:3])#[N:22]

Participants

5

Reactant 3

HCID 6329Methylamine2×HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 129515272-{[(3-Bromopyridin-2-yl)methyl]sulfanyl}ethan-1-amine

Product 1

HCID 53848828HCID 53848828, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sequential reaction of dimethylcyanodithioimidocarbonate with 2-((2-aminoethyl)thiomethyl)-3-bromopyridine) and excess methylamine at room temperature in ethanol, the methylamine being added after initial standing overnight and the solution then allowed to stand for a further four hours, followed by chromatographic purification on a column of silica gel with elution by ethyl acetate and final recrystallisation from ethyl acetate-petroleum ether gave N-cyano-N'-[2-((3-bromo-2-pyridyl)methylthio)ethyl]-N"-methylguanidine m.p. 114°-116°.

Workup

  1. waitto stand for a further four hours
  2. customfollowed by chromatographic purification on a column of silica gel with elution by ethyl acetate
  3. customfinal recrystallisation from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-aa72ff1005a94025a06584965be363c9
Source dataset
uspto-grants-1976_12
Patent number
US04000302

Reaction notes

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