Potassium Carbonate → HCID 178485057, compound

HRID 1277881Notes

Reaction equation

HRID 1277881 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]([CH2:10][C:11]1[O:15][C:14]([CH2:16][S:17][CH2:18][CH2:19][NH2:20])=[CH:13][CH:12]=1)[CH3:9].CS[C:23](=[N:27][CH3:28])[NH:24][C:25]#[N:26]>C(#N)C.[N+]([O-])([O-])=O.[Ag+]>[C:25]([N:24]=[C:23]([NH:27][CH3:28])[NH:20][CH2:19][CH2:18][S:17][CH2:16][C:14]1[O:15][C:11]([CH2:10][N:8]([CH3:7])[CH3:9])=[CH:12][CH:13]=1)#[N:26]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1111031-Cyano-2,3-dimethylisothioureaHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine

Product 1

HCID 178485057HCID 178485057, compoundYield 2.4%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6342AcetonitrileSolvent2×

Procedure

To a stirred suspension of potassium carbonate (20.7 g) in a solution of 2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethanamine (10.7 g) and N-cyano-N'-methylcarbamimidothioic acid methyl ester (7.1 g) in acetonitrile (107 ml) at 70° was added a solution of silver nitrate (9.35 g) in acetonitrile (20 ml) during 1 hr. The mixture was stirred for 16 hr, the solid filtered and the filtrate evaporated to dryness. The residue was dissolved in ethyl acetate (250 ml). A portion of this (10.5 ml) was washed with water (6 ml), the ethyl acetate layer evaporated to give a solid which was crystallised from isopropylacetate (1.75 ml) giving N"-cyano-N-[2-[[[5-(dimethylaminomethyl)-2-furanyl]methyl]thio]ethyl]-N'-methylguanidine (0.35 g) m.p. 79°-81.5°.

Workup

  1. filtrationthe solid filtered
  2. customthe filtrate evaporated to dryness
  3. dissolutionThe residue was dissolved in ethyl acetate (250 ml)
  4. washA portion of this (10.5 ml) was washed with water (6 ml)
  5. customthe ethyl acetate layer evaporated
  6. customto give a solid which
  7. customwas crystallised from isopropylacetate (1.75 ml)

Sources & evidence

ORD record
ord-2bdae766b7c147169caa193c207f1809
Source dataset
uspto-grants-1981_07
Patent number
US04279819

Reaction notes

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