Hydrochloric Acid → HCID 11148202, compound

HRID 336333Notes

Reaction equation

HRID 336333 reaction equation
[OH-:1].[Na+].[Cl:3][C:4]1[C:5](F)=[C:6]([CH:10]=[CH:11][C:12]=1[F:13])[C:7]([OH:9])=[O:8].Cl>CN1CCN(C)C1=O>[Cl:3][C:4]1[C:5]([OH:1])=[C:6]([CH:10]=[CH:11][C:12]=1[F:13])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27735323-Chloro-2,4-difluorobenzoic acid

Product 1

HCID 11148202HCID 11148202, compound

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
140 °C

Procedure

Sodium hydroxide (208 g, 5.21 mol) was added in portions to a stirred solution of 3-chloro-2,4-difluorobenzoic acid (200 g, 1.04 mol) in 1,3-dimethyl imidazolidin-2-one (1 L), and the mixture was heated to 140° C. for 2 hours. The reaction mixture was cooled to room temperature and neutralized with ice-cooled 2N HCl (350 mL) precipitating a white solid that was collected by filtration. The filtered solid was dissolved in methyl t-butyl ether (500 mL), washed with saturated brine solution (150 mL) and dried over Na2SO4. Removal of solvent under vacuum afforded the title compound as off white solid. Yield: 180 g (91%). 1H NMR (300 MHz, MeOH-d4) δ: 6.8 (t, 1H), 7.90 (dd, 1H), 11.3 (s, 1H). MS (ES) MH−: 189 for C7H4ClFO3.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature and neutralized with ice-
  2. customprecipitating a white solid
  3. filtrationthat was collected by filtration
  4. dissolutionThe filtered solid was dissolved in methyl t-butyl ether (500 mL)
  5. washwashed with saturated brine solution (150 mL)
  6. dry with materialdried over Na2SO4
  7. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-0e1e57af7fd845b2a3088bed4cd00da9
Source dataset
uspto-grants-2014_11
Patent number
US08889671B2

Reaction notes

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