Guanidine Hydrochloride → HCID 178508992, compound

HRID 1507771Notes

Reaction equation

HRID 1507771 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[F:6][C:7]1[CH:26]=[CH:25][C:10]([C:11]([NH:13][CH:14]([C:20](OCC)=[O:21])[C:15](OCC)=[O:16])=[O:12])=[CH:9][CH:8]=1.[Na]>C(O)C>[NH2:4][C:3]1[N:5]=[C:15]([OH:16])[C:14]([NH:13][C:11](=[O:12])[C:10]2[CH:25]=[CH:26][C:7]([F:6])=[CH:8][CH:9]=2)=[C:20]([OH:21])[N:2]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 33239760HCID 33239760, compound

Product 1

HCID 178508992HCID 178508992, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Guanidine hydrochloride (1.35 g, 14.1 mmol) and diethyl 2-(4-fluorobenzamido)malonate (example 1, 3.0 g, 10.1 mmol) were added to a solution of sodium (0.46 g, 20.2 mmol) in ethanol (50 ml). The reaction mixture was refluxed for 3 hours. The reaction was cooled down to room temperature. The solid product was filtered off and washed with ethanol. The product was dissolved in a minimal volume of water and acidified to pH 4-5 with 5M HCl. The precipitate was collected, washed with water and dried to give the title compound as a white solid (1.41 g, 53%).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. filtrationThe solid product was filtered off
  3. washwashed with ethanol
  4. dissolutionThe product was dissolved in a minimal volume of water
  5. customThe precipitate was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-133ccc626b2f4870858740802c757215
Source dataset
uspto-grants-2015_12
Patent number
US09221822B2

Reaction notes

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