Hydrochloric Acid → HCID 178483280, compound

HRID 482658Notes

Reaction equation

HRID 482658 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][C:15]#[N:16])[CH:6]=1)[CH3:3].C(Cl)(Cl)Cl.Cl.[S:22]([NH2:26])([NH2:25])(=[O:24])=[O:23]>CO>[S:22]([NH:26][C:15](=[NH:16])[CH2:14][CH2:13][S:12][CH2:11][C:7]1[CH:6]=[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])[CH:10]=[CH:9][N:8]=1)(=[O:24])(=[O:23])[NH2:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 82267SulfamideHCID 198704133-[({4-[(Dimethylamino)methyl]pyridin-2-yl}methyl)sulfanyl]propanenitrile

Product 1

HCID 178483280HCID 178483280, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-(4-Dimethylaminomethyl-2-pyridylmethylthio)propionitrile in a mixture of dry methanol and dry chloroform under nitrogen at 2° C. is treated with dried hydrogen chloride gas and allowed to stand at ca. 0° C. to give after basification with ice cold potassium carbonate solution methyl-3-(4-dimethylaminomethyl-2-pyridylmethylthio)propionimidate which is reacted in methanol with sulphamide under reflux. Evaporation of the solvent at reduced pressure and purification of the product by chromatography yields N-sulphamoyl-3-(4-dimethylaminomethyl-2-pyridylmethylthio)propionamidine.

Workup

  1. customto stand at ca. 0° C.
  2. customto give after basification with ice cold potassium carbonate solution methyl-3-(4-dimethylaminomethyl-2-pyridylmethylthio)propionimidate which
  3. temperatureunder reflux
  4. customEvaporation of the solvent
  5. customat reduced pressure and purification of the product by chromatography

Sources & evidence

ORD record
ord-95071697d3b04f27bdd22ffee558ca57
Source dataset
uspto-grants-1986_03
Patent number
US04574126

Reaction notes

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