Potassium Carbonate → HCID 178484977, compound

HRID 465040Notes

Reaction equation

HRID 465040 reaction equation
Br.Br.[NH2:3][CH2:4][CH2:5][S:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]2[N:12]=[CH:13][NH:14][C:10]=2[CH:9]=1.NCCCOC1C=C[C:25]2[N:26]=[C:27]([NH:29][C:30](N)=[NH:31])NC=2C=1.C(C#N)(=N)SC.C(C#N)(=N)SC.C(=O)([O-])[O-].[K+].[K+]>CO>[C:30]([NH:29][C:27]([NH:26][CH3:25])=[N:3][CH2:4][CH2:5][S:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]2[N:12]=[CH:13][NH:14][C:10]=2[CH:9]=1)#[N:31]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 20261654HCID 20261654, compoundHCID 86740389HCID 86740389, compoundHCID 178512598HCID 178512598, compound

Product 1

HCID 178484977HCID 178484977, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A methanol solution (50 ml) containing 5-[(2-aminoethyl)thiomethyl]benzimidazole.dihydrobromide (4.2 g) prepared in item (A) above, dimethyl dithiocyanoimidocarbonate (1.75 g) and potassium carbonate (1.65 g) was agitated for 16 hrs at room temperature. After removal of the solid component, the solvent was distilled off. Then, a 20% methylamine in methanol (45 ml) was added to the residue, and the mixture was agitated for 16 hrs at room temperature. The solvent was distilled off under reduced pressure, and the oily residue was subjected to column chromatography using silica gel as a filler and an ethyl acetate/methanol (7:1) mixture as a developer. Then, N-cyano-N'-methyl-N"-[2-(5-benzimidazolylmethylthio)ethyl]guanidine (mp. 191.4° C., 2.46 g, 75%) was obtained.

Workup

  1. customAfter removal of the solid component
  2. distillationthe solvent was distilled off
  3. additionThen, a 20% methylamine in methanol (45 ml) was added to the residue
  4. stirringthe mixture was agitated for 16 hrs at room temperature
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1f62667e6acf4405914cefbbb8d8e294
Source dataset
uspto-grants-1985_10
Patent number
US04550118

Reaction notes

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