Triethylamine → 4-Bromo-N-(2-(phenylamino)phenyl)benzamide

HRID 1422454Notes

Reaction equation

HRID 1422454 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:11]1([NH:17][C:18]2[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[NH:17][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68297N-Phenyl-o-phenylenediamineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 230940554-Bromo-N-(2-(phenylamino)phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-benzoyl chloride (11 g, 50 mmol) in anhydrous dichloromethane (DCM) (100 ml), was added N-phenylbenzene-1,2-diamine (10.2 g, 55 mmol), then triethylamine (17 ml, 122 mmol) slowly. The whole mixture was then stirred at room temperature (r.t.) overnight. Subsequent filtration gave a white solid (Compound 8) (6.5 g). The filtrate was worked up with water (300 ml), and then extracted with DCM (300 ml) three times. The resulting organic phase was collected and dried over MgSO4, concentrated and recrystallized in DCM/hexanes to give another portion of white solid (Compound 8) (10.6 g). The total amount of product (Compound 8) was 17.1 g, in 93% yield.

Workup

  1. filtrationSubsequent filtration

Sources & evidence

ORD record
ord-22c186137a55489ea8f769b2e35db6ff
Source dataset
uspto-grants-2015_01
Patent number
US08927121B2

Reaction notes

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