Acetic Anhydride → HCID 178471894, compound

HRID 47894Notes

Reaction equation

HRID 47894 reaction equation
[F:1][C:2]1[C:7]([C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[C:6]([F:16])[C:5]([F:17])=[C:4]([F:18])[C:3]=1[F:19].[CH:20](OCC)(OCC)OCC.C(OC(=O)C)(=O)C.[CH:37]1([NH2:40])[CH2:39][CH2:38]1>>[F:1][C:2]1[C:7]([C:8]([C:10](=[CH:20][NH:40][CH:37]2[CH2:39][CH2:38]2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[C:6]([F:16])[C:5]([F:17])=[C:4]([F:18])[C:3]=1[F:19]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 69828CyclopropylamineHCID 2760255Ethyl (pentafluorobenzoyl)acetate

Product 1

HCID 178471894HCID 178471894, compoundYield 72%

Procedure

70.5 g of ethyl pentafluorobenzoylacetate (0.25 mol), 66.6 g of triethyl orthoformate (0.45 mol) and 77.4 g of diacetyl oxide (0.72 mol) were stirred at 150° C. for 2.5 hours. Fractions having a lower boiling point were evaporated under reduced pressure. To the residue was added 250 ml of anhydrous ethanol. 14.5 g of cyclopropylamine (0.25 mol) was added to the solution under cooling of ice water and the reaction was then carried out at room temperature for 2 hours. The resultingt mixture was filtered under suction. The residue was re-crystallized from a mixture of petroleum ether and cyclohexane to yield 62.8 g (0.18 mol) of ethyl 2-(pentafluorobenzoyl)-3-cyclopropylaminoacrylate in 72.0% yield, mp 88-91° C.

Workup

  1. customwere evaporated under reduced pressure
  2. additionTo the residue was added 250 ml of anhydrous ethanol
  3. filtrationThe resultingt mixture was filtered under suction
  4. customThe residue was re-crystallized from a mixture of petroleum ether and cyclohexane

Sources & evidence

ORD record
ord-eebf0d28d11f4d49bc6bf0f742331807
Source dataset
uspto-grants-2004_03
Patent number
US06699992B2

Reaction notes

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