Acetic Anhydride → HCID 178471883, compound

HRID 47897Notes

Reaction equation

HRID 47897 reaction equation
[Cl:1][C:2]1[C:15]([F:16])=[C:14]([Cl:17])[C:13]([F:18])=[C:12]([Cl:19])[C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH:20](OCC)(OCC)OCC.C(OC(=O)C)(=O)C.[CH:37]1([NH2:40])[CH2:39][CH2:38]1>>[Cl:1][C:2]1[C:15]([F:16])=[C:14]([Cl:17])[C:13]([F:18])=[C:12]([Cl:19])[C:3]=1[C:4]([C:6](=[CH:20][NH:40][CH:37]1[CH2:39][CH2:38]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 69828CyclopropylamineHCID 86589177Ethyl 2,4,6-trichloro-3,5-difluorobenzoylacetate

Product 1

HCID 178471883HCID 178471883, compoundYield 74.8%

Procedure

82.9 g of ethyl 2,4,6-trichloro-3,5-difluorobenzoylacetate (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 at room temperature for 2 hours. The resultant mixture was filtered under suction. The residue was re-crystallized from a mixture of petroleum ether and cyclohexane to yield 74.5 g (0.187 mol) of ethyl 2-(2,4,6-trichloro-3,5-difluorobenzoyl)-3-cyclopropylaminoacrylate in 74.6% yield.

Workup

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

Sources & evidence

ORD record
ord-b89926daf4454c288be859258652d887
Source dataset
uspto-grants-2004_03
Patent number
US06699992B2

Reaction notes

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