Acetic Anhydride → HCID 178500746, compound

HRID 47888Notes

Reaction equation

HRID 47888 reaction equation
[Cl:1][C:2]1[C:14]([O:15][CH3:16])=[C:13]([Cl:17])[C:12]([F:18])=[CH:11][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH3:10])=[O:8])=[O:5].[CH:19](OCC)(OCC)OCC.C(OC(=O)C)(=O)C.[CH:36]1([NH2:39])[CH2:38][CH2:37]1>>[Cl:1][C:2]1[C:14]([O:15][CH3:16])=[C:13]([Cl:17])[C:12]([F:18])=[CH:11][C:3]=1[C:4]([C:6](=[CH:19][NH:39][CH:36]1[CH2:38][CH2:37]1)[C:7]([O:9][CH3:10])=[O:8])=[O:5]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 69828CyclopropylamineHCID 86589174Methyl 2,4-dichloro-5-fluoro-3-methoxybenzoylacetate

Product 1

HCID 178500746HCID 178500746, compoundYield 72.9%

Procedure

73.8 g of methyl 2,4-dichloro-5-fluoro-3-methoxybenzoylacetate (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 re-crystallized from a mixture of petroleum ether and cyclohexane to yield 66.0 g (0.182 mol) of methyl 2-(2,4-dichloro-5-fluoro-3-methoxybenzoyl)-3-cyclopropylaminoacrylate in 72.9% 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 re-crystallized from a mixture of petroleum ether and cyclohexane

Sources & evidence

ORD record
ord-5eaba4de37424051a6939add821f6ef0
Source dataset
uspto-grants-2004_03
Patent number
US06699992B2

Reaction notes

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