Ammonium Hydroxide → HCID 57467466, compound

HRID 1890793Notes

Reaction equation

HRID 1890793 reaction equation
[F:1][C:2]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:3]=1[O:4][C:5]([CH3:10])([CH3:9])[C:6](O)=[O:7].CC[N:18]=C=NCCCN(C)C.Cl.[OH-].[NH4+]>C(Cl)Cl>[F:1][C:2]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:3]=1[O:4][C:5]([CH3:10])([CH3:9])[C:6]([NH2:18])=[O:7]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 15318012-(2,4-difluorophenoxy)-2-methylpropanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57467466HCID 57467466, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,4-difluorophenoxy)-2-methylpropanoic acid (10.0 g, 46.3 mmol, Chembridge) in methylene chloride (200 mL) were added 1-hydroxybenzotriaole hydrate (8.5 g, 55.5 mmol, Aldrich), N-(3-dimethylaminopropyl)-N-ethylcarbodimide hydrochloride (10.6 g, 55.5 mmol, Aldrich) and ammonium hydroxide (54.0 g, 463 mmol). The reaction mixture was stirred at room temperature for 16 hours and then quenched with water (100 mL). The aqueous layer was extracted with methylene chloride (3×100 mL). The combined organic extracts were washed with brine, 5% citric acid, and brine (100 mL each), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to obtain the titled compound. MS (ESI+) m/z 233 (M+NH4)+.

Workup

  1. customquenched with water (100 mL)
  2. extractionThe aqueous layer was extracted with methylene chloride (3×100 mL)
  3. washThe combined organic extracts were washed with brine, 5% citric acid, and brine (100 mL each)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e9bcaedc02ed4d96ab6dbe1cce32478d
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

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