Guanidine Hydrochloride → HCID 178508987, compound

HRID 1492144Notes

Reaction equation

HRID 1492144 reaction equation
[Na].Cl.[NH2:3][C:4]([NH2:6])=[NH:5].[F:7][CH:8]([C:14](OCC)=[O:15])[C:9](OCC)=[O:10]>C(O)C>[F:7][C:8]1[C:9]([OH:10])=[N:5][C:4]([NH2:6])=[N:3][C:14]=1[OH:15]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 12702Diethyl fluoromalonateHCID 5360545Sodium2×

Product 1

HCID 178508987HCID 178508987, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (257 mg, 11 mmol) was dissolved in absolute ethanol (50 ml) with stirring under argon. When the sodium had thoroughly dissolved, guanidine hydrochloride (2) (502 mg, 5 mmol) and diethyl fluoromalonate (1) (790 mg, 4.4 mmol) were added. The solution was left to stir at room temperature overnight. A condenser was then attached to the flask and the solution was refluxed under argon for 4.5 hours. The solution was cooled to room temperature and concentrated. The residue was redissolved in 20 ml hot H2O and acidified to pH 4. The mixture was cooled on ice and the precipitate was collected, yielding (3) as a peach colored solid (618 mg, 96%): MS (70 eV, EI)m/z (relative intensity) 146(M+, 100), 18 (95), 172 (26), 17 (24), 300 (21); IR (mull, cm-1) 3363, 1695, 1601, 1420, 1208, 677, 666; UV (MeOH, nm) 206(3,840), 235(3,380), 270(11,600). Exact Mass Calcd for C4H4N3O2F: 146.0366. Found: 146.0371.

Workup

  1. waitThe solution was left
  2. stirringto stir at room temperature overnight
  3. customA condenser was then attached to the flask
  4. temperaturethe solution was refluxed under argon for 4.5 hours
  5. concentrationconcentrated
  6. dissolutionThe residue was redissolved in 20 ml hot H2O
  7. temperatureThe mixture was cooled on ice
  8. customthe precipitate was collected

Sources & evidence

ORD record
ord-9cd323dd959a40df8b37ad451a4a594e
Source dataset
uspto-grants-1994_12
Patent number
US05373012

Reaction notes

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