Potassium Carbonate → N-ethyl-N-phenyl-o-(2,6-dichloroanilino)phenylacetamide

HRID 894403Notes

Reaction equation

HRID 894403 reaction equation
[CH2:1]([N:3]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1Br)[CH3:2].[Cl:20][C:21]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:22]=1[NH2:23].C(=O)([O-])[O-].[K+].[K+]>C1(C)C(C)=CC=CC=1.[Cu]>[CH2:1]([N:3]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:23][C:22]1[C:21]([Cl:20])=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:28])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 118462,6-DichloroanilineHCID 12884243N-ethyl-N-phenyl-(o-bromophenyl)acetamide

Product 1

HCID 12884244N-ethyl-N-phenyl-o-(2,6-dichloroanilino)phenylacetamideYield 77.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 6.36 g (0.02 mole) of N-ethyl-N-phenyl-(o-bromophenyl)acetamide having a boiling point of 185° to 190° C. under 2 mmHg, 6.48 g (0.04 mole) of 2,6-dichloroaniline, 3.0 g (0.02 mole) of anhydrous potassium carbonate, 2.0 g of copper powder and 2.0 g of cuprous bromide was reacted in 100 ml of xylene in the same manner as in Example 22 to obtain 6.1 g of a colorless prism having a melting point of 121° to 123° C. The yield was 77.4%.

Workup

  1. customto obtain 6.1 g of a colorless prism

Sources & evidence

ORD record
ord-880d727506954c17884fd4f70af46584
Source dataset
uspto-grants-1981_08
Patent number
US04283532

Reaction notes

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