Hydrochloric Acid → HCID 59228900, compound

HRID 2389224Notes

Reaction equation

HRID 2389224 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH:5]1[CH:9]=[CH:8][CH:7]=[CH:6]1.[Cl:10][C:11]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:12]=1[C:13](Cl)=[O:14].Cl>ClCCl>[Cl:10][C:11]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:12]=1[C:13]([C:6]1[NH:5][CH:9]=[CH:8][CH:7]=1)=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8027PyrroleHCID 179452,5-Dichlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 59228900HCID 59228900, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

200 mL of dichloromethane was poured into a 1 L three-necked flask equipped with a stirrer, thermometer, dropping funnel, and nitrogen inlet tube, cooled to 0° C. using a salt-ice bath, and then 80.4 g (0.6 mol) of aluminum chloride and 40.3 g (0.6 mol) of pyrrole were added. Next, 104.7 g (0.50 mol) of 2,5-dichlorobenzoyl chloride dissolved in 100 mL of dichloromethane was slowly added dropwise using a dropping funnel. After completing the addition, the reactant was stirred for 3 hours while maintained at 5° C. to 10° C. using the salt-ice bath. After confirming the disappearance of raw materials by way of thin-layer chromatography, the reaction liquid was gradually added to 1 L of 2 N HCl, and excessive aluminum chloride was dissolved and removed. The organic layer was washed using 5% sodium bicarbonate water, water, and a sodium chloride solution, and the organic layer was dried using magnesium sulfate, and then the solvent was removed by an evaporator. The approximate yield amount was 120 g. The crude product was recrystallized from hexane/ethyl acetate to obtain the intended product in an amount of 95 g and at a yield of 79% as a milky white solid.

Workup

  1. customequipped with a stirrer
  2. additionwas slowly added dropwise
  3. additionthe addition
  4. temperaturewhile maintained at 5° C. to 10° C.
  5. customthe reaction liquid
  6. dissolutionwas dissolved
  7. customremoved
  8. washThe organic layer was washed
  9. dry with materiala sodium chloride solution, and the organic layer was dried
  10. customthe solvent was removed by an evaporator
  11. customThe crude product was recrystallized from hexane/ethyl acetate
  12. customto obtain the intended product in an amount of 95 g

Sources & evidence

ORD record
ord-a09d8f49f4ee45f59fd8703ac6c8a8bb
Source dataset
uspto-grants-2012_09
Patent number
US08273499B2

Reaction notes

Loading…