Formic Acid → HCID 12782780, compound

HRID 1659324Notes

Reaction equation

HRID 1659324 reaction equation
[CH:1]([OH:3])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.C(N1C=CN=C1)=O.[Cl:23][C:24]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:30]=2[Cl:36])=[CH:27][NH:26][CH:25]=1>O1CCCC1>[Cl:23][C:24]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:30]=2[Cl:36])=[CH:27][N:26]([CH:1]=[O:3])[CH:25]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 110838321H-imidazole-1-carboxaldehyde2×HCID 128838083-Chloro-4-(2,3-dichlorophenyl)-1H-pyrrole

Product 1

HCID 12782780HCID 12782780, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

5 ml of a solution of 0.7 g of formic acid (99%) in tetrahydrofuran was added dropwise to a solution of 2.3 g of carbodiimidazole in 50 ml of tetrahydrofuran at room temperature with stirring to prepare the solution of 1-formylimidazole. A solution of 1g of 3-chloro-4-(2,3-dichlorophenyl) pyrrole in 10 ml of tetrahydrofuran was added dropwise to the solution of 1-formylimidazole. After refluxing the solution for two hours with stirring, the resulting reaction solution was left overnight and then the solvent was removed by distillation under reduced pressure. The residue was dissolved in 100 ml of ethyl acetate and the solution was washed with water and then saturated aqueous solution of sodium chloride. After drying the solution with anhydrous magnesium sulfate, the solvent was removed by distillation to obtain 1.1 g of the desired product. The product was purified by recrystallization from ethyl acetate to obtain colorless needles of the desired compound.

Workup

  1. temperatureAfter refluxing the solution for two hours
  2. stirringwith stirring
  3. customthe resulting reaction solution
  4. customthe solvent was removed by distillation under reduced pressure
  5. dissolutionThe residue was dissolved in 100 ml of ethyl acetate
  6. washthe solution was washed with water
  7. dry with materialAfter drying the solution with anhydrous magnesium sulfate
  8. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-f6494d1aaf0b49e2af2b47f347b5bf40
Source dataset
uspto-grants-1981_12
Patent number
US04303667

Reaction notes

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