Diethyl fluoromalonate → HCID 178433477, compound

HRID 2290616Notes

Reaction equation

HRID 2290616 reaction equation
[Na].Cl.[C:3]([NH2:6])(=[NH:5])[CH3:4].[F:7][CH:8]([C:14](OCC)=[O:15])[C:9](OCC)=[O:10]>>[CH3:4][C:3]1[N:6]=[C:14]([OH:15])[C:8]([F:7])=[C:9]([OH:10])[N:5]=1

Participants

4

Reactant 3

HCID 12702Diethyl fluoromalonateHCID 67170Acetamidine monohydrochlorideHCID 5360545Sodium

Product 1

HCID 178433477HCID 178433477, compound

Conditions

Temperature
23 °C

Procedure

According to the procedure of J. Chem. Soc. 1959, 3286, a solution of 0.92 g (40 mmol) of sodium metal dissolved in 20 mL of methaol was treated with 2.08 g (22 mmol) of acetamidine hydrochloride. After 5 minutes, to this stirred mixture was added 3.6 g (20 mmol) of diethyl fluoromalonate. The reaction mixture was heated to reflux for 18 hours, cooled to 23° C., and then concentrated in vacuo. The residue was dissolved in water, neutralized with aqueous 3N HCl (6 mL), and chilled. A precipitate which formed was isolated by filtration and triturated with a 1:1 mixture of diethyl ether/ethyl acetate. The resulting crude product (1.36 g, 47%) was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 hours
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in water
  5. temperaturechilled
  6. customA precipitate which formed
  7. customwas isolated by filtration
  8. customtriturated with a 1:1 mixture of diethyl ether/ethyl acetate
  9. customThe resulting crude product (1.36 g, 47%) was used without further purification

Sources & evidence

ORD record
ord-24851d60a742487a8c983d97aea15bb0
Source dataset
uspto-grants-1986_10
Patent number
US04617393

Reaction notes

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