Guanidine Hydrochloride → HCID 178508736, compound

HRID 846386Notes

Reaction equation

HRID 846386 reaction equation
[Na].Cl.[NH2:3][C:4]([NH2:6])=[NH:5].C([O:9][C:10](=O)[CH:11]([C:20]#[N:21])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=1[Cl:19])C>C(O)C>[NH2:5][C:4]1[N:6]=[C:20]([NH2:21])[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])=[C:10]([OH:9])[N:3]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 5360545Sodium2×HCID 19705040HCID 19705040, compound

Product 1

HCID 178508736HCID 178508736, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (1.2 g, 0.052 mol) was added in portions to absolute ethanol (50 ml) with stirring. After the sodium had dissolved guanidine hydrochloride (3.69 g, 0.039 mol) was added followed by ethyl-2-cyano-2-(2,3-dichlorophenyl)acetate (5 g, 0.0195 mol). The mixture was refluxed for 8 hours, EtOH was removed under reduced pressure and the residue was partitioned between EtOAc and water. The EtOAc layer was extracted with 2N NaOH and the extract was neutralised with 2N HCl with cooling. The precipitated solid was filtered and dried to give the title compound. (0.22 g), mp. 275° C. (decomp).

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed for 8 hours
  3. customEtOH was removed under reduced pressure
  4. customthe residue was partitioned between EtOAc and water
  5. extractionThe EtOAc layer was extracted with 2N NaOH
  6. temperaturewith cooling
  7. filtrationThe precipitated solid was filtered
  8. customdried

Sources & evidence

ORD record
ord-427dd7b7173b487f98d365e01e116308
Source dataset
uspto-grants-1992_08
Patent number
US05136080

Reaction notes

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