Dimethylformamide → HCID 178484998, compound

HRID 2071940Notes

Reaction equation

HRID 2071940 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH3:8])SC)#[N:2].[CH3:9][C:10]1[NH:14][CH:13]=[N:12][C:11]=1[CH2:15][S:16][CH2:17][CH2:18][NH2:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>N1C=CC=CC=1.[N+]([O-])([O-])=O.[Ag+]>[C:1]([NH:3][C:4]([NH:7][CH3:8])=[N:19][CH2:18][CH2:17][S:16][CH2:15][C:11]1[N:12]=[CH:13][NH:14][C:10]=1[CH3:9])#[N:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1111031-Cyano-2,3-dimethylisothioureaHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazole

Product 1

HCID 178484998HCID 178484998, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 1049PyridineSolvent

Procedure

A solution of N-cyano-N', S-dimethylisothiourea (0.81 g) and silver nitrate (1.06 g) in pyridine (100 ml) was added to a stirred mixture of 2-((5-methyl-4-imidazolyl)methylthio)-ethylamine (1.07 g), anhydrous potassium carbonate (0.44 g) and anhydrous dimethylformamide (4ml). The mixture was stirred at room temperature for 18 hours and filtered. The filtrate was evaporated to dryness and the residue was eluted from a column of silica gel using isopropyl alcoholethylacetate (1:4) followed by isopropyl alcohol-ethyl acetate (1:3) to give N-cyano-N'-methyl-N"-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]guanidine (0.71 g) m.p. 139°-141° C.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness
  3. washthe residue was eluted from a column of silica gel

Sources & evidence

ORD record
ord-65aaffe10a42450d923fc0ef88dbf4c6
Source dataset
uspto-grants-1977_09
Patent number
US04049671

Reaction notes

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