Triethylamine → N-Benzyloxy-2-(2,4-difluoroanilino)-4,5-difluoro-benzamide

HRID 2270253Notes

Reaction equation

C(N1C=CN=C1)(N1C=CN=C1)=O.[F:13][C:14]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:15]=1[NH:16][C:17]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:18]=1[C:19]([OH:21])=O.Cl.[CH2:34]([O:41][NH2:42])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(N(CC)CC)C>C1COCC1>[CH2:34]([O:41][NH:42][C:19](=[O:21])[C:18]1[CH:22]=[C:23]([F:27])[C:24]([F:26])=[CH:25][C:17]=1[NH:16][C:15]1[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:14]=1[F:13])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Carbonyldiimidazole (3.1 g, 19.1 mmol) was added to a suspension of 2-(2,4-difluoroanilino)-4,5-difluorobenzoic acid (Example H-4, 4.54 g, 15.9 mmol) in 120 mL of THF, and the mixture was stirred for 24 hours at 25° C. O-Benzylhydroxylamine hydrochloride (2.54 g, 15.9 mmol) and triethylamine (2.66 mL, 19.1 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 5.66 g of the title compound as an oil.

Workup

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

Sources & evidence

ORD record: ord-9d0aa35a333b4a1fa66018920b6e4486
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06331538B1

Reaction notes

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