HCID 178503877, compound → HCID 178433311, compound

HRID 2166718Notes

Reaction equation

HRID 2166718 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])SC)#[N:2]>CN(C)C=O.[N+]([O-])([O-])=O.[Ag+]>[C:1]([NH:3][C:4]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])#[N:2]

Participants

4

Reactant 1

HCID 178503877HCID 178503877, compound

Product 1

HCID 178433311HCID 178433311, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A solution of silver nitrate (3.06 g.) in dimethyl formamide (20 ml.) was added to a solution of N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-S-methyl isothiourea (4.9 g.) in dimethylformamide (30 ml.). The resultant solution was kept at room temperature for 1 hour cooled and filtered to remove silver methylmercaptide, 4-methyl-5-((2-aminoethyl)thiomethyl)imidazole (3.07 g.) in dimethyl formamide (10 ml.) was added and this solution was heated overnight on the steam bath. Concentration followed by chromatographic purification of the product on a column of silica gel afforded the title compound (1.2 g.), m.p. 90°-94°, containing a small amount of water.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customto remove silver methylmercaptide, 4-methyl-5-((2-aminoethyl)thiomethyl)imidazole (3.07 g.) in dimethyl formamide (10 ml.)
  4. additionwas added
  5. temperaturethis solution was heated overnight on the steam bath
  6. concentrationConcentration
  7. customfollowed by chromatographic purification of the product on a column of silica gel

Sources & evidence

ORD record
ord-65d9c91cd4fc447e92ebfe2b79331924
Source dataset
uspto-grants-1983_06
Patent number
US04388319

Reaction notes

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