Benzenamine, 2-chloro-4-fluoro- → [2-Chloro-4-(2-chloro-4-fluoro-phenylamino)-phenyl]-(2-methyl-5-nitro-phenyl)-methanone

HRID 2067213Notes

Reaction equation

HRID 2067213 reaction equation
ClC1C=C(NC2C=CC(C(F)(F)F)=CC=2)C=CC=1C(C1C=C([N+]([O-])=O)C=CC=1C)=O.Br[C:32]1[CH:37]=[CH:36][C:35]([C:38]([C:40]2[CH:45]=[C:44]([N+:46]([O-:48])=[O:47])[CH:43]=[CH:42][C:41]=2[CH3:49])=[O:39])=[C:34]([Cl:50])[CH:33]=1.[Cl:51][C:52]1[CH:58]=[C:57]([F:59])[CH:56]=[CH:55][C:53]=1[NH2:54]>>[Cl:50][C:34]1[CH:33]=[C:32]([NH:54][C:53]2[CH:55]=[CH:56][C:57]([F:59])=[CH:58][C:52]=2[Cl:51])[CH:37]=[CH:36][C:35]=1[C:38]([C:40]1[CH:45]=[C:44]([N+:46]([O-:48])=[O:47])[CH:43]=[CH:42][C:41]=1[CH3:49])=[O:39]

Participants

4

Reactant 3

HCID 75013Benzenamine, 2-chloro-4-fluoro-HCID 11494123(4-Bromo-2-chloro-phenyl)-(2-methyl-5-nitro-phenyl)-methanoneHCID 68419760[2-Chloro-4-(4-trifluoromethyl-phenylamino)-phenyl]-(2-methyl-5-nitro-phenyl)-methanone

Product 1

HCID 68421804[2-Chloro-4-(2-chloro-4-fluoro-phenylamino)-phenyl]-(2-methyl-5-nitro-phenyl)-methanone

Procedure

The reaction was carried out similarly as described in the preparation of compound 414, using compound 402 (0.28 mmol) and 2-chloro-4-fluoroaniline (0.28 mmol). The crude product was purified by continuous gradient flash chromatography using MeOH/EtOAc 0:100 to 25:75 as the eluent to afford the title compound as yellow foam.

Workup

  1. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-19986c6ce60e407290a13c37251c2fdb
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

Loading…