Bromobenzene → HCID 13643796, compound

HRID 1982065Notes

Reaction equation

HRID 1982065 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH3:13])=[CH:7][C:6]=1[O:14][CH2:15][CH3:16])(=O)[CH3:2].Br[C:18]1[CH:23]=CC=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+]>[Cu].II.C1(C)C=CC=CC=1.C(O)CC(C)C>[C:1]1([NH:4][C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH3:13])=[CH:7][C:6]=2[O:14][CH2:15][CH3:16])[CH:20]=[CH:19][CH:18]=[CH:23][CH:2]=1

Participants

9

Reactant 4

HCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 23318500N-(2,4-Diethoxyphenyl)acetamide

Product 1

HCID 13643796HCID 13643796, compoundYield 70%

Reagents, catalysts & solvents 4

HCID 807IodineCatalystHCID 23978CopperCatalystHCID 1140TolueneSolventHCID 31260Isoamyl AlcoholSolvent

Procedure

To a mixture of 66.9 g of N-acetyl-2,4-diethoxyaniline and 70.7 g of bromobenzene, 29 g of anhydrous potassium carbonate, 2.1 g of copper powder and 0.8 g of iodine were added, and the mixture was reacted at a temperature of from 170° to 180° C. for 20 hours. Then, to this reaction mixture, 30 g of potassium hydroxide and 100 ml of isoamylalcohol were added, and the mixture was reacted at a temperature from 120° to 130° C. for 3 hours. Then, 300 ml of toluene was added thereto. The toluene layer was washed with water, separated by liquid separation, concentrated and then purified by distillation under reduced pressure, whereby 54 g of oily N-phenyl-2,4-di-ethoxyaniline was obtained. The boiling point of this product was from 180° to 185° C./3 mmHg.

Workup

  1. additionwere added
  2. customthe mixture was reacted at a temperature of from 170° to 180° C. for 20 hours
  3. customthe mixture was reacted at a temperature from 120° to 130° C. for 3 hours
  4. washThe toluene layer was washed with water
  5. customseparated by liquid separation
  6. concentrationconcentrated
  7. distillationpurified by distillation under reduced pressure

Sources & evidence

ORD record
ord-419a376e5c084455900401bdca32e8dc
Source dataset
uspto-grants-1986_06
Patent number
US04594601

Reaction notes

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