Formamidine acetate → HCID 178522470, compound

HRID 718265Notes

Reaction equation

HRID 718265 reaction equation
C(O)(=O)C.[CH:5]([NH2:7])=[NH:6].[F:8][C:9]1[CH:26]=[CH:25][C:12]([C:13]([NH:15][CH:16]([C:21](OC)=[O:22])[C:17](OC)=[O:18])=[O:14])=[CH:11][CH:10]=1.[Na]>C(O)C>[OH:22][C:21]1[C:16]([NH:15][C:13](=[O:14])[C:12]2[CH:25]=[CH:26][C:9]([F:8])=[CH:10][CH:11]=2)=[C:17]([OH:18])[N:7]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 5360545SodiumHCID 66758678Dimethyl 2-(4-fluorobenzamido)malonate

Product 1

HCID 178522470HCID 178522470, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Formamidine acetate (0.46 g, 4.46 mmol) and dimethyl 2-(4-fluorobenzamido)malonate (1.0 g, 3.71 mmol) were added to a solution of sodium (0.17 g, 7.43 mmol) in ethanol (37 ml). The reaction mixture was refluxed for 3 hours. After cooling down, the precipitate 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 yield the title compound as a white solid (0.60 g, 64%).

Workup

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

Sources & evidence

ORD record
ord-f9f2c0cb64ea4e0eb587204686337bdb
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

Loading…