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

HRID 2067257Notes

Reaction equation

HRID 2067257 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8]C2C=CC(C(F)(F)F)=CC=2)[CH:5]=[CH:4][C:3]=1[C:19]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[CH3:30])=[O:20].BrC1C=CC(C(C2C=C([N+]([O-])=O)C=CC=2C)=O)=C(Cl)C=1.[Cl:51][C:52]1[CH:57]=[CH:56][C:55](N)=[C:54]([CH3:59])[CH:53]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:55]2[CH:56]=[CH:57][C:52]([Cl:51])=[CH:53][C:54]=2[CH3:59])[CH:5]=[CH:4][C:3]=1[C:19]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[CH3:30])=[O:20]

Participants

4

Reactant 3

HCID 72514-Chloro-2-toluidineHCID 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 68416515[2-Chloro-4-(4-chloro-2-methyl-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 (0.56 mmol) and 4-chloro-2-methyl-phenylamine (0.56 mmol). The crude product was purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) 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-06f00b1fcd6842f88f28e53df93bdad6
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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