Acetic Anhydride → HCID 178471869, compound

HRID 47891Notes

Reaction equation

HRID 47891 reaction equation
[C:1]([C:3]1[C:4]([Cl:19])=[C:5]([CH:14]=[C:15]([F:18])[C:16]=1[Cl:17])[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])#[N:2].[CH:20](OCC)(OCC)OCC.C(OC(=O)C)(=O)C.[CH:37]1([NH2:40])[CH2:39][CH2:38]1>>[C:1]([C:3]1[C:4]([Cl:19])=[C:5]([CH:14]=[C:15]([F:18])[C:16]=1[Cl:17])[C:6]([C:8](=[CH:20][NH:40][CH:37]1[CH2:39][CH2:38]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])#[N:2]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 69828CyclopropylamineHCID 86589175Ethyl 3-cyano-2,4-dichloro-5-fluorobenzoylacetate

Product 1

HCID 178471869HCID 178471869, compoundYield 70.1%

Procedure

76.0 g of ethyl 3-cyano-2,4-dichloro-5-fluorobenzoylacetate (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 and the reaction was then carried out for 2 hours. The resulting mixture was filtered under suction. The residue was recrystallized from a mixture of petroleum ether and cyclohexane to yield 65.0 g (0.175 mol) of ethyl 2-(3-cyano-2,4-dichloro-5-fluorobenzoyl)-3-cyclopropylaminoacrylate in 70.1% yield.

Workup

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

Sources & evidence

ORD record
ord-670782c6bd174e549333fde5e909bd54
Source dataset
uspto-grants-2004_03
Patent number
US06699992B2

Reaction notes

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