4-Bromo-3-fluoroaniline → 4-(3-(4-bromo-3-fluorophenyl)ureido)-N,N-dimethyl-benzamide

HRID 2092525Notes

Reaction equation

ClC(Cl)(Cl)CO[C:5](=[O:18])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:17])[N:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=1.[Br:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][C:23]=1[F:29]>C1(C)C=CC=CC=1>[Br:21][C:22]1[CH:28]=[CH:27][C:25]([NH:26][C:5](=[O:18])[NH:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]([N:14]([CH3:15])[CH3:16])=[O:17])=[CH:11][CH:12]=2)=[CH:24][C:23]=1[F:29]

Participants

Conditions

Temperature: 110 °C

Procedure

To a 250 mL round bottom flask, 2,2,2-trichloroethyl(4-(dimethylcarbamoyl)phenyl)carbamate (30 g, 0.0885 mol), 4-bromo-3-fluoroaniline (20 g, 0.1062 mol), TEA (24.6 mL, 0.177 mol) and toluene (150 mL) was added. The reaction mixture was maintained at 110° C. for 12 h. The reaction mass was cooled to room temperature. The obtained precipitate was collected by filtration and dried under vacuum to get the desired product [15 g, 50%]. 1H NMR (300 MHz, DMSO-d6): δ 9.09 (s, 1H), 8.99 (s, 1H), 7.65-7.53 (m, 2H), 7.49 (d, J=8.4 Hz, 2H), 7.35 (d, J=8.4 Hz, 2H), 7.14 (d, J=8.4 Hz, 1H), 2.93 (s, 6H); LC-MS (ESI): Calculated mass: 379.0; Observed mass: 382.1 (RT: 1.43 min).

Workup

temperatureThe reaction mass was cooled to room temperature
filtrationThe obtained precipitate was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-5339bedcfc774b66af8fa242cc3b5934
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440662B2

Reaction notes

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