1,2-Dichloroethane → N-(2-amino-3-bromo-6-methoxy-phenyl)-4-isopropyl-benzamide

HRID 1661886Notes

Reaction equation

HRID 1661886 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([NH2:10])[C:3]=1[NH2:11].C(Cl)CCl.[CH:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)([CH3:18])[CH3:17]>CN(C1C=CN=CC=1)C.ClCCl>[NH2:11][C:3]1[C:2]([Br:1])=[CH:7][CH:6]=[C:5]([O:8][CH3:9])[C:4]=1[NH:10][C:23](=[O:24])[C:22]1[CH:26]=[CH:27][C:19]([CH:16]([CH3:17])[CH3:18])=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 108204-Isopropylbenzoic AcidHCID 577720123-Bromo-6-methoxybenzene-1,2-diamine

Product 1

HCID 57772045N-(2-amino-3-bromo-6-methoxy-phenyl)-4-isopropyl-benzamideYield 98.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 870 mg (4.01 mmol) 3-bromo-6-methoxy-benzene-1,2-diamine, 1.16 g (6.0 mmol) EDC, 744 mg (6.0 mmol) DMAP and 707 mg (4.01 mmol) 4-isopropylbenzoic acid in 20 ml dichloromethane is stirred at room temperature for 72 h. The reaction mixture is concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=2:1) to afford 1.44 g of the title compound as a slightly reddish solid.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=2:1)

Sources & evidence

ORD record
ord-b273ba08849647efb1897d5806e0e3bd
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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