Acetamidine monohydrochloride → HCID 136043557, compound

HRID 1742023

Reaction equation

HRID 1742023 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].[F:6][C:7]([F:20])([C:16]([F:19])([F:18])[F:17])[C:8]([CH2:10][C:11](OCC)=[O:12])=O>CCO>[CH3:3][C:2]1[NH:5][C:11](=[O:12])[CH:10]=[C:8]([C:7]([F:6])([F:20])[C:16]([F:17])([F:18])[F:19])[N:4]=1

Participants

4

Reactant 2

HCID 67170Acetamidine monohydrochlorideHCID 522203Ethyl 4,4,5,5,5-Pentafluoro-3-oxovalerate

Product 1

HCID 136043557HCID 136043557, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Na (2.3 g, 0.1 mol) in EtOH (125 mL) was mixed with acetamidine hydrochloride (4.72 g, 50 mmol) and the reaction mixture was stirred for 15 min. Ethyl pentafluoropropionylacetate (11.7 g, 50 mmol) was added and the reaction mixture was refluxed for 6 h. The solvent was removed in vacuo, and the residue was taken up in H2O and acidified with dilute HCl to pH 2. The aqueous solution was extracted with EtOAc and the organic layer was dried over Na2SO4, then evaporated to afford 6 g of a yellowish solid. The crude product was purified by flash chromatography (CHCl3 containing MeOH 0% to 4%) to provide 2 g (17.5% yield) of a solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 6 h
  2. customThe solvent was removed in vacuo
  3. extractionThe aqueous solution was extracted with EtOAc
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-74bdcbd4ca6548bdb9315a916f76d485
Source dataset
uspto-grants-1994_08
Patent number
US05336677

Linked notes

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