Hydrochloric Acid → HCID 15545159, compound

HRID 2185627Notes

Reaction equation

HRID 2185627 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]2=[O:29])=[CH:12][C:3]=1[O:4][C:5]1([C:8]([O:10]C)=[O:9])[CH2:7][CH2:6]1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[N:19]([CH3:28])[C:18]2=[O:29])=[CH:12][C:3]=1[O:4][C:5]1([C:8]([OH:10])=[O:9])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11154830HCID 11154830, compound

Product 1

HCID 15545159HCID 15545159, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.0 g of methyl 1-[2-chloro-4-fluoro-5-{3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl}phenoxy]cyclopropanecarboxylate was dissolved in a solution consisting of 10 ml of 1,4-dioxane and 10 ml of conc. hydrochloric acid, and the obtained solution was heated under reflux for 2 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution in turn, and dried over anhydrous magnesium sulfate. The resultant was concentrated under reduced pressure. The produced crystals was washed with a mixted solution of hexane and t-butyl methyl ether to give 1.2 g of 1-[2-chloro-4-fluoro-5-{3-methyl-2,6-dioxo-4-(trifluoro-methyl)-1,2,3,6-tetrahydropyrimidin-1-yl}phenoxy]cyclo-propanecarboxylic acid (Compound 1-1).

Workup

  1. temperaturethe obtained solution was heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride solution in turn
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe resultant was concentrated under reduced pressure
  7. washThe produced crystals was washed with a mixted solution of hexane and t-butyl methyl ether

Sources & evidence

ORD record
ord-bc2ea7a6055f4d3bb702eac224a4b20d
Source dataset
uspto-grants-2002_06
Patent number
US06403534B1

Reaction notes

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