Aniline → HCID 178498354, compound

HRID 1695536Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[C:6]([C:11](Cl)=[N:12][OH:13])[C:5]=1[F:15].[F:17][C:18]([F:27])([F:26])[C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].NC1C=CC=CC=1>C1COCC1>[Cl:10][C:9]1[C:4]([C:3]([O:2][CH3:1])=[O:16])=[C:5]([F:15])[C:6]([C:11](=[N:12][OH:13])[NH:22][C:21]2[CH:23]=[CH:24][CH:25]=[C:19]([C:18]([F:17])([F:26])[F:27])[CH:20]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl-6-chloro-3-(chloro(hydroxyimino)methyl)-2-fluorobenzoate (1.2 g, 4.3 mmol) in THF (10 ml) at 0° C. was added 3-(trifluoromethyl)aniline (2.7 ml, 22 mmol). After stirring at 0° C. for 10 min, the reaction was allowed to warm to RT and stir for 3 h, then heat at 50° C. in an oil bath overnight. Added more of the aniline (5 mL) and heated at 50° C. for another 5 h. After cooling to RT, the solvent was evaporated and solid formed was filtered off. The filtrate was dissolved in DCM and purified by chromatography through a Redi-Sep® pre-packed silica gel column (120 g), eluting with a gradient of 5% to 25% EtOAc in hexane, to provide methyl 6-chloro-2-fluoro-3-(N′-hydroxy-N-(3-(trifluoromethyl)phenyl)carbamimidoyl)benzoate as off-white solid.

Workup

temperatureto warm to RT
stirringstir for 3 h
temperatureheat at 50° C. in an oil bath overnight
temperatureheated at 50° C. for another 5 h
temperatureAfter cooling to RT
customthe solvent was evaporated
customsolid formed
filtrationwas filtered off
dissolutionThe filtrate was dissolved in DCM
custompurified by chromatography through a Redi-Sep® pre-packed silica gel column (120 g)
washeluting with a gradient of 5% to 25% EtOAc in hexane

Sources & evidence

ORD record: ord-57bb25ad6b6f4430b0299509aeeb9e94
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163742B2

Reaction notes

Loading…