Hydrochloric Acid → HCID 178478776, compound

HRID 247372Notes

Reaction equation

HRID 247372 reaction equation
[ClH:1].[C:2]([NH:4][C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH: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][N:12]=[CH:11][CH:10]=1)=[NH:6])(=[O:18])[NH2:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 178512372HCID 178512372, compound

Product 1

HCID 178478776HCID 178478776, compound

Procedure

Concentrated HCl (21 ml) is added to a mixture of 1-cyano-3-(4-pyridylmethyl)guanidine (10.0 g) in 500 ml of isopropanol. A pale yellow precipitate forms. The stirred suspension is heated on a steam bath and boiled for ten minutes. The solvent is evaporated under reduced pressure and the residual solid treated with 25 ml of concentrated HCl. The solution is heated on a steam bath for several minutes and diluted with isopropanol (50 ml) and allowed to cool. The resulting solid is collected and dred in air, extracted into 900 ml of methanol, which is filtered, and concentrated on a not plate. The hot solution is diluted with ethyl acetate and concentrated further. A white precipitate forms on cooling which is collected and dried in air giving the desired amidinourea dihydrochloride, MP 208°-209.5° C. w/dec.

Workup

  1. temperatureThe stirred suspension is heated on a steam bath
  2. waitboiled for ten minutes
  3. customThe solvent is evaporated under reduced pressure
  4. additionthe residual solid treated with 25 ml of concentrated HCl
  5. temperatureThe solution is heated on a steam bath for several minutes
  6. additiondiluted with isopropanol (50 ml)
  7. temperatureto cool
  8. customThe resulting solid is collected
  9. extractionextracted into 900 ml of methanol, which
  10. filtrationis filtered
  11. concentrationconcentrated on a not plate
  12. additionThe hot solution is diluted with ethyl acetate
  13. concentrationconcentrated further
  14. temperatureA white precipitate forms on cooling which
  15. customis collected
  16. customdried in air

Sources & evidence

ORD record
ord-4587d4f870214b558b680908cb45799e
Source dataset
uspto-grants-1987_11
Patent number
US04707478

Reaction notes

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