Guanidine Hydrochloride → HCID 178508948, compound

HRID 234931Notes

Reaction equation

HRID 234931 reaction equation
[Na].Cl.[NH2:3][C:4]([NH2:6])=[NH:5].CC[O:9][C:10]([CH:12]([C:21](OCC)=[O:22])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])=O>C(O)C>[NH2:5][C:4]1[N:6]=[C:10]([OH:9])[C:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])=[C:21]([OH:22])[N:3]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 2736112Diethyl 2-(2,4-dichlorophenyl)malonateHCID 5360545Sodium2×

Product 1

HCID 178508948HCID 178508948, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (4.529, 0.196M) was added in portions to ethanol (150 ml). After all the sodium had dissolved guanidine hydrochloride (12.44 g, 0.13M) was added followed by diethyl 2,4-dichlorophenyl malonate(20 g, 0.0655M). The mixture was refluxed for 6 hours, EtOH was removed under reduced pressure and the residue partitioned between 2N NaOH (400 ml) and EtOAc (400 ml). The aqueous layer was acidified with concentrated hydrochloric acid with cooling and the precipitated solid was filtered and dried (11 g, 62%).

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed for 6 hours
  3. customEtOH was removed under reduced pressure
  4. customthe residue partitioned between 2N NaOH (400 ml) and EtOAc (400 ml)
  5. temperaturewith cooling
  6. filtrationthe precipitated solid was filtered
  7. customdried (11 g, 62%)

Sources & evidence

ORD record
ord-fb67323acd574468835d688d0803dbe7
Source dataset
uspto-grants-1997_01
Patent number
US05597827

Reaction notes

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