Anisole → HCID 178462746, compound

HRID 649498Notes

Reaction equation

HRID 649498 reaction equation
[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][C:5]2[N:6]([CH2:10][CH3:11])[C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1.[Br:15][CH2:16][CH2:17][N:18]1[C:22](=[O:23])[CH2:21][CH2:20][C:19]1=[O:24].C1(OC)C=CC=CC=1>C(OCC)(=O)C>[Br-:15].[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][C:5]2[N+:6]([CH2:10][CH3:11])=[C:7]([CH3:9])[N:8]([CH2:16][CH2:17][N:18]3[C:22](=[O:23])[CH2:21][CH2:20][C:19]3=[O:24])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 767171H-Benzimidazole, 5,6-dichloro-1-ethyl-2-methyl-HCID 135613951-(2-Bromoethyl)pyrrolidine-2,5-dione

Product 1

HCID 178462746HCID 178462746, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

11.5 g of 5,6-dichloro-1-ethyl-2-methylbenzoimidazole and 20.6 g of N-(2-bromoethyl)succinimide were put into a 200-ml three-necked flask equipped with a stirrer and a reflux condenser and heated for 2 hours on an oil bath which has been heated to a temperature of 130° C. 10 ml of anisole was added to the mixture. The admixture was then allowed to stand for cooling. 50 ml of ethyl acetate was added to the admixture. The admixture was then refluxed for 30 minutes. After being allowed to cool to room temperature, the resulting crystal was filtered off, washed with acetone, and then dried at a temperature of 50° C. for 5 hours. Yield: 18.7 g (86%).

Workup

  1. customequipped with a stirrer and a reflux condenser
  2. temperatureheated for 2 hours on an oil bath which
  3. temperaturefor cooling
  4. temperatureThe admixture was then refluxed for 30 minutes
  5. temperatureto cool to room temperature
  6. filtrationthe resulting crystal was filtered off
  7. washwashed with acetone
  8. customdried at a temperature of 50° C. for 5 hours

Sources & evidence

ORD record
ord-86e8fa36df7b4279be13c2ee187f9e9b
Source dataset
uspto-grants-1988_04
Patent number
US04740455

Reaction notes

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