Ethylamine → HCID 178464589, compound

HRID 2419078Notes

Reaction equation

HRID 2419078 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.[CH2:21]([NH2:23])[CH3:22]>>[C:7]([NH:6][C:3]([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:23][CH2:21][CH3:22])#[N:8]

Participants

4

Reactant 3

HCID 6341EthylamineHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 129515272-{[(3-Bromopyridin-2-yl)methyl]sulfanyl}ethan-1-amine

Product 1

HCID 178464589HCID 178464589, compound

Procedure

Sequential reaction of dimethylcyanodithioimidocarbonate with 2-((2-aminoethyl)thiomethyl)-3-bromopyridine and excess ethylamine, followed by chromatographic purification on a column of silica gel with elution by ethyl acetate and final recrystallisation from ethyl acetate-petroleum ether afforded N-cyano-N'-[2-((3-bromo-2-pyridyl)methylthio)-ethyl]-N"-ethylguanidine, m.p. 123°-124°. (Found: C, 42.2; H, 4.7; N, 20.5; S, 9.4; C12H16Br N5S. requires: C, 42.1; H, 4.7; N, 20.5; S, 9.4).

Workup

  1. customfollowed by chromatographic purification on a column of silica gel with elution by ethyl acetate
  2. customfinal recrystallisation from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-285d5c7d670844fc8000386044cf2886
Source dataset
uspto-grants-1978_08
Patent number
US04104382

Reaction notes

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