Triethylamine → N-cyano-N'-[2-[[[2-furanyl]methyl]thio]ethyl]-N"-methylguanidine

HRID 65767Notes

Reaction equation

HRID 65767 reaction equation
[C:1]([NH:3][C:4](SC)=[N:5][CH3:6])#[N:2].C(N(CC)CC)C.[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH2:21][S:22][CH2:23][CH2:24][NH2:25]>CN(C)C=O.CO.[N+]([O-])([O-])=O.[Ag+]>[C:1]([NH:3][C:4]([NH:25][CH2:24][CH2:23][S:22][CH2:21][C:17]1[O:16][CH:20]=[CH:19][CH:18]=1)=[N:5][CH3:6])#[N:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 1111031-Cyano-2,3-dimethylisothioureaHCID 1189702-(Furfurylthio)ethylamine

Product 1

HCID 53954457N-cyano-N'-[2-[[[2-furanyl]methyl]thio]ethyl]-N"-methylguanidineYield 34.7%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of silver nitrate (8.25 g) in dimethylformamide (50 ml) was added dropwise to a solution of N-cyano-N'-methylcarbamimidothioic acid, methyl ester (6.1 g), triethylamine (4.8 g) and 2-[[[2-furanyl]methyl]thio]ethanamine (7.8 g) in methanol (150 ml). After 42 hr at 50° the mixture was filtered and the filtrate evaporated. The residue was partitioned between ethyl acetate and water. The organic layers were dried and evaporated to give an oil which yielded crystalline N-cyano-N'-[2-[[[2-furanyl]methyl]thio]ethyl]-N"-methylguanidine (3.9 g) m.p. 78°-82°.

Workup

  1. filtrationAfter 42 hr at 50° the mixture was filtered
  2. customthe filtrate evaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic layers were dried
  5. customevaporated
  6. customto give an oil which

Sources & evidence

ORD record
ord-317570242a8c4a838cacab684ca4bc30
Source dataset
uspto-grants-1978_12
Patent number
US04128658

Reaction notes

Loading…