1-Cyano-2,3-dimethylisothiourea → N-cyano-N'-[2-[[[5-(methylamino)methyl-2-furanyl]methyl]thio]ethyl]-N"-methylguanidine

HRID 65754Notes

Reaction equation

HRID 65754 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[O:8][C:7]([CH2:9][S:10][CH2:11][CH2:12][NH2:13])=[CH:6][CH:5]=1.[C:14]([NH:16][C:17](SC)=[N:18][CH3:19])#[N:15]>>[C:14]([NH:16][C:17]([NH:13][CH2:12][CH2:11][S:10][CH2:9][C:7]1[O:8][C:4]([CH2:3][NH:2][CH3:1])=[CH:5][CH:6]=1)=[N:18][CH3:19])#[N:15]

Participants

3

Reactant 2

HCID 1111031-Cyano-2,3-dimethylisothioureaHCID 202094925-[[(2-Aminoethyl)thio]methyl]-N-methyl-2-furanmethanamine

Product 1

HCID 53722477N-cyano-N'-[2-[[[5-(methylamino)methyl-2-furanyl]methyl]thio]ethyl]-N"-methylguanidineYield 38.6%

Procedure

A mixture of 2-[[[5-(methylamino)methyl-2-furanyl]methyl]thio]ethanamine (2.0 g) and N-cyano-N'-methylcarbamimidothioic acid, methyl ester (1.25 g) was heated on a steam bath for 6.5 hr. Vacuum was applied at regular intervals to remove methanethiol. The crude product was purified by column chromatography Rf 0.65 (silica/methanol:ammonia 79:1) to give N-cyano-N'-[2-[[[5-(methylamino)methyl-2-furanyl]methyl]thio]ethyl]-N"-methylguanidine (1.05 g) m.p. 81°-85°.

Workup

  1. temperaturewas heated on a steam bath for 6.5 hr
  2. customto remove methanethiol
  3. customThe crude product was purified by column chromatography Rf 0.65 (silica/methanol:ammonia 79:1)

Sources & evidence

ORD record
ord-89ff67722fce4d3b811bdb6c4b7085a5
Source dataset
uspto-grants-1978_12
Patent number
US04128658

Reaction notes

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