2,4-Dichloro-6-nitroaniline → HCID 45381090, compound

HRID 1402800Notes

Reaction equation

HRID 1402800 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([N+:10]([O-])=O)[C:3]=1[NH2:4].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:26][C:25](=O)[O:24][C:22](=[O:23])[CH2:21]2)=[CH:16][CH:15]=1>O1CCOCC1>[Cl:9][C:7]1[CH:8]=[C:2]([Cl:1])[C:3]2[N:4]=[C:25]([CH2:26][CH:20]([C:17]3[CH:16]=[CH:15][C:14]([Cl:13])=[CH:19][CH:18]=3)[CH2:21][C:22]([OH:24])=[O:23])[NH:10][C:5]=2[CH:6]=1.[ClH:1]

Participants

4

Reactant 2

HCID 758932,4-Dichloro-6-nitroanilineHCID 1046394-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione

Product 1

HCID 45381090HCID 45381090, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The solution of commercial 2,4-dichloro-6-nitroaniline (621 mg) and 3-(4-chlorophenyl)glutaric anhydride (674 mg) in 1,4-dioxane (2 ml) was heated to reflux shortly and stirred at rt for 1 h. The solvent was removed by distillation and the residue dried in vacuo. The oily residue was dissolved in acetic acid (6 ml) and heated to reflux. Iron powder (1.01 g) was added and the mixture stirred under reflux for 1 h. Then conc. HCl (6 ml) was added cautiously and the green-yellow solution was refluxed for additional 2 h. All volatiles were removed at the water aspirator and the residue precipitated from acetic acid/conc. HCl solution with water. The solid was collected by suction filtration and washed well with 1M HCl and water. The crude was recrystallised from acetic acid to give 4-(5,7-dichloro-2-benzimidazolyl)-3-(4-chlorophenyl)butanoic acid•HCl (325 mg) as colourless crystals.

Workup

  1. temperatureto reflux shortly
  2. customThe solvent was removed by distillation
  3. customthe residue dried in vacuo
  4. dissolutionThe oily residue was dissolved in acetic acid (6 ml)
  5. temperatureheated to reflux
  6. additionIron powder (1.01 g) was added
  7. stirringthe mixture stirred
  8. temperatureunder reflux for 1 h
  9. additionThen conc. HCl (6 ml) was added cautiously
  10. temperaturethe green-yellow solution was refluxed for additional 2 h
  11. customAll volatiles were removed at the water aspirator
  12. customthe residue precipitated from acetic acid/conc
  13. filtrationThe solid was collected by suction filtration
  14. washwashed well with 1M HCl and water
  15. customThe crude was recrystallised from acetic acid

Sources & evidence

ORD record
ord-76c1f99472d542f0ad0dddeb12ef637e
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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