Hydrogen Sulfide → HCID 18919508, compound

HRID 1682689Notes

Reaction equation

HRID 1682689 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9][C:6]2=[N:7][CH:8]=1)#[N:2].[SH2:17]>N1C=CC=CC=1.C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9][C:6]2=[N:7][CH:8]=1)(=[S:17])[NH2:2]

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 10632490HCID 10632490, compound

Product 1

HCID 18919508HCID 18919508, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

Ethyl 5-cyanofuro[2,3-b]pyridine-2-carboxylate (773 mg, 4.14 mmol) was dissolved in a mixed solvent of pyridine (40 ml) and triethylamine (8 ml), and a hydrogen sulfide gas was blown in for 10 minutes. The mixture was stirred at room temperature for 14 hours. The solvent was distilled away from the reaction mixture under reduced pressure to give ethyl 5-thiocarbamoylfuro[2,3-b]pyridine-2-carboxylate as a yellow solid. Acetone (80 ml) and methyl iodide (8.0 ml) were added and the mixture was refluxed under heating for one hour. Low boiling matters were distilled away from the reaction mixture under reduced pressure to give ethyl 5-[(1-methylthio)-iminomethyl]furo[2,3-b]pyridine-2-carboxylate. Methanol (80 ml) and ammonium acetate (694 mg, 9.00 mmol) were added and the mixture was refluxed under heating for 3.5 hours. Low boiling matters were distilled away from the reaction mixture under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol=97/3-4/1) to give 2.05 g of ethyl 5-amidinofuro[2,3-b]pyridine-2-carboxylate hydrochloride as a yellow solid (69% in 3 steps).

Workup

  1. customwas blown in for 10 minutes
  2. distillationThe solvent was distilled away from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-e0bd11f2f4a048f0bc8108e82f1163bb
Source dataset
uspto-grants-1997_06
Patent number
US05635527

Reaction notes

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