Triethylamine → HCID 15908874, compound

HRID 2270159Notes

Reaction equation

HRID 2270159 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[F:13][C:14]1[CH:15]=[C:16]([NH2:24])[C:17](=[CH:21][C:22]=1[F:23])[C:18]([OH:20])=O.Cl.[CH2:26]([O:33][NH2:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C>C1COCC1>[NH2:24][C:16]1[CH:15]=[C:14]([F:13])[C:22]([F:23])=[CH:21][C:17]=1[C:18]([NH:34][O:33][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 102312Benzyloxyamine hydrochlorideHCID 7359652-Amino-4,5-difluorobenzoic acid

Product 1

HCID 15908874HCID 15908874, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Carbonyldiimidazole (6.1 g, 37 mmol) was added to a suspension of 4,5-difluoroanthranilic acid (5.40 g, 31 mmol) in 250 mL of THF, and the mixture was stirred for 24 hours at 25° C. O-benzylhydroxylamine hydrochloride (4.95 g, 31 mmol) and triethylamine (5.2 mL, 37 mmol) were added, and the mixture was heated to reflux for 4 hours. The reaction mixture was concentrated and washed with 1N HCl, saturated NaHCO3, brine, and dried over magnesium sulfate. The solution was concentrated to give 6.0 g of the title compound as a solid, mp 125-126° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated
  4. washwashed with 1N HCl, saturated NaHCO3, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-b87bd4e56e3f4940a5a54954d3250853
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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