Hydrochloric Acid → HCID 178478774, compound

HRID 247374Notes

Reaction equation

HRID 247374 reaction equation
[ClH:1].[C:2]([NH:4][C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[NH:6])#[N:3].C([OH:18])(C)C>>[ClH:1].[ClH:1].[C:2]([NH:4][C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[NH:6])(=[O:18])[NH2:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 178512370HCID 178512370, compound

Product 1

HCID 178478774HCID 178478774, compound

Procedure

Concentrated HCl (15.4 ml) is added to a stirred solution of 1-cyano-3-(2-pyridylmethyl)guanidine (4.50 g) in 310 ml of isopropanol. The reaction mixture is stirred at room temperature overnight. The solvent is concentrated in vacuo and the residue treated with 1.8 liters of boiling ethanol. The resulting suspension is stirred and heated while adding small portions of water until most of the solid has dissolved. The solution is filtered through Celite, diluted to 2 liters with absolute ethanol and concentrated on a hot plate and cooled. The first crop of crystals, MP 214°-215° C. w/dec, and the second crop of crystals, MP 215°-216° C. w/dec, obtained by concentration of the filtrate, were combined to give 2.60 g of the carbamoyl guanidine as a grey-green solid. The grey-green solid is dissolved in boiling ethanol, treated with Darco G-60 and filtered. The filtrate is boiled down on a hotplate and the white crystalline precipitate is collected, washed with absolute ethanol and dried in air yielding 1.77 g of the desired product MP 214°-216° C. w/dec.

Workup

  1. concentrationThe solvent is concentrated in vacuo
  2. additionthe residue treated with 1.8 liters of boiling ethanol
  3. stirringThe resulting suspension is stirred
  4. temperatureheated
  5. additionwhile adding small portions of water until most of the solid
  6. dissolutionhas dissolved
  7. filtrationThe solution is filtered through Celite
  8. additiondiluted to 2 liters with absolute ethanol
  9. concentrationconcentrated on a hot plate
  10. temperaturecooled
  11. customobtained by concentration of the filtrate

Sources & evidence

ORD record
ord-1609e4bf55004409b885993cc2e0d51a
Source dataset
uspto-grants-1987_11
Patent number
US04707478

Reaction notes

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