Triethylamine → 181371-35-7

HRID 1851076Notes

Reaction equation

HRID 1851076 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:18](OCC)(=[O:23])[CH2:19][C:20]([CH3:22])=O>CO>[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:18](=[O:23])[CH:19]=[C:20]([CH3:22])[NH:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8868Ethyl AcetoacetateHCID 699814-Fluorophenylhydrazine hydrochloride

Product 1

HCID 341367181371-35-7Yield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(4-Fluorophenyl)hydrazine hydrochloride (20.0 g, 0.123 mol) was added to a solution of triethylamine (20.5 mL) in methanol (350 mL). Then, a solution of ethyl acetoacetate (16.0 g, 0.123 mol) in methanol (50 mL) was added. The resulting reaction mixture was stirred for 4 hours under reflux and extracted with dichloromethane and sodium chloride aqueous solution. The aqueous layer was extracted again with dichloromethane. All the organic layers were collected, dried with Na2SO4 and then filtered. The filtrate was concentrated. The resulting residue was purified by silica gel chromatography (ethyl acetate:hexane=1:2). The target compound was yielded (21.0 g, 89% yield).

Workup

  1. customThe resulting reaction mixture
  2. temperatureunder reflux
  3. extractionextracted with dichloromethane and sodium chloride aqueous solution
  4. extractionThe aqueous layer was extracted again with dichloromethane
  5. customAll the organic layers were collected
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customThe resulting residue was purified by silica gel chromatography (ethyl acetate:hexane=1:2)
  10. customThe target compound was yielded (21.0 g, 89% yield)

Sources & evidence

ORD record
ord-c385529294994b03b0d51b2d6cd04da4
Source dataset
uspto-grants-2015_02
Patent number
US08957102B2

Reaction notes

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