Ethanol, reaction products with ammonia, distn. residues → HCID 178508377, compound

HRID 406307Notes

Reaction equation

HRID 406307 reaction equation
[NH3:1].C(O)C.Cl.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:19][CH2:20][CH2:21]Cl)[C:14](=[NH:18])OCC)=[C:9]([C:23]([F:26])([F:25])[F:24])[CH:8]=1>>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:19][CH2:20][CH2:21][NH:1][C:14]2=[NH:18])=[C:9]([C:23]([F:26])([F:25])[F:24])[CH:8]=1

Participants

3

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 86662647HCID 86662647, compound

Product 1

HCID 178508377HCID 178508377, compound

Procedure

A saturated ammonia-ethanol solution (2.5 mL) was added to ethyl 2-(4-bromo-2-trifluoromethylphenyl)-5-chloropentanimidate hydrochloride obtained in Preparation Example 3-1 (500 mg), and the mixture was stirred at room temperature for eight days. The insoluble matter was removed by filtration and then the filtrate was concentrated under reduced pressure. Methylene chloride and a 1 N sodium hydroxide solution were added to the resulting residue, and the organic layer was separated. The aqueous layer was reextracted with methylene chloride. The combined organic layers were dried over anhydrous potassium carbonate and concentrated under reduced pressure to obtain 320 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customThe insoluble matter was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionMethylene chloride and a 1 N sodium hydroxide solution were added to the resulting residue
  4. customthe organic layer was separated
  5. dry with materialThe combined organic layers were dried over anhydrous potassium carbonate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88956008ba59481aa90a9a42a5697d5f
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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