Dimethyl N-cyanodithioiminocarbonate → HCID 178503889, compound

HRID 370580Notes

Reaction equation

HRID 370580 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[C:5]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[O:13][C:14]([CH2:17][N:18]([CH3:20])[CH3:19])=[CH:15][CH:16]=1)=[O:6].[CH3:24][S:25][C:26](SC)=[N:27][C:28]#[N:29]>C(O)C>[C:28]([N:27]=[C:26]([S:25][CH3:24])[NH:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[C:5]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[O:13][C:14]([CH2:17][N:18]([CH3:19])[CH3:20])=[CH:15][CH:16]=1)=[O:6])#[N:29]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 13269217HCID 13269217, compound

Product 1

HCID 178503889HCID 178503889, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 20 g of 3-amino-N-[2-(5-dimethylaminomethylfuran-2-ylmethylthio)ethyl]benzamide and 8.8 g of dimethyl cyanodithioiminocarbonate in 150 ml of absolute ethanol is heated with reflux for 30 hours, then it is concentrated under reduced pressure and the crude oil thus obtained is poured on a silica column and eluted with a mixture chloroform:methanol 4:1. The fairly pure fractions are collected and the solvent is evaporated under reduced pressure. Thus, 6.5 g of 3-(3-cyano-2-methylisothioureido)-N-[2-(5-dimethylaminomethylfuran-2-ylmethylthio)ethyl]benzamide are obtained as an oil which is mixed with 10 ml of a 33% solution of methylamine in ethanol. The mixture thus obtained is left to stand 48 hours at room temperature, then the excess of methylamine is eliminated under reduced pressure. Thus 5 g of an oil are obtained which is submitted to a flash chromatography on silica by eluting with a mixture chloroform:ethanol 1:1. The pure fractions are collected and evaporated, the residue is crystallized twice from isopropanol. Thus, 2.5 g of 3-(2-cyano-3-methylguanidino)-N-[2-(5-dimethylaminomethylfuran-2-ylmethylthio)ethyl]benzamide are obtained; m.p. 140°-142° C.

Workup

  1. temperatureis heated
  2. temperaturewith reflux for 30 hours
  3. concentrationit is concentrated under reduced pressure
  4. customthe crude oil thus obtained
  5. additionis poured on a silica column
  6. washeluted with a mixture chloroform:methanol 4:1
  7. customThe fairly pure fractions are collected
  8. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-85960da6f7584fba9f5c1dc576ff1282
Source dataset
uspto-grants-1985_07
Patent number
US04526995

Reaction notes

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