Hydrochloric Acid → 4-(4-Amino-phenoxy)-N-(4-bromo-phenyl)-3-nitro-benzamide

HRID 605294

Reaction equation

HRID 605294 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13](Cl)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)=[CH:4][CH:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.[OH-].[K+].Cl>CS(C)=O.O>[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:13]2[CH:14]=[CH:15][C:10]([C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[O:20])=[CH:11][C:12]=2[N+:17]([O-:19])=[O:18])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4034-AminophenolHCID 14797Potassium HydroxideHCID 1068537N-(4-bromophenyl)-4-chloro-3-nitrobenzamide

Product 1

HCID 670405064-(4-Amino-phenoxy)-N-(4-bromo-phenyl)-3-nitro-benzamideYield 98.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the product from Example 10A (3.55g, 10 mmol), 4-aminophenol (1.09 g, 10 mmol), and potassium hydroxide (1.12 g, 20 mmol) were dissolved in dimethyl sulfoxide (15 mL) and heated at 100° C. in a CEM Discover microwave for 25 minutes. The mixture was then cooled to room temperature, poured into water (300 mL), the pH of the solution adjusted to 6 with 1N aqueous hydrochloric acid, the resultant solution stirred for 30 minutes and the resultant solid collected and dried to provide the title compound as a yellow solid (4.2 g, 98%).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customthe resultant solid collected
  3. customdried

Sources & evidence

ORD record
ord-d3d78c4f4fe34b559b89262890ea832d
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Linked notes

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