HCID 23363108, compound → HCID 23363131, compound

HRID 1081871Notes

Reaction equation

HRID 1081871 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N+:14]([O-])=O)=[C:11]([CH:13]=2)[NH2:12])=[C:4]([CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH:3]=1>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([NH2:14])=[C:11]([NH2:12])[CH:13]=2)=[C:4]([CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH:3]=1

Participants

4

Reactant 1

HCID 23363108HCID 23363108, compound

Product 1

HCID 23363131HCID 23363131, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

5-[4-Chloro-2-(1H-1,2,4-triazol-1-ylmethyl)phenoxy]-2-nitroaniline (11 g) from Example 37 was dissolved in acetic acid (100 ml), followed by gradual addition of zinc powder (12.5 g) under water cooling. After the addition, insoluble materials were filtered off, and the filtrate was concentrated under reduced pressure. To the residue was added ethyl acetate, and to the resulting solution was added carefully saturated sodium hydrogen carbonate solution to make the solution alkaline. The organic phase was washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was crystallized from chloroform (100 ml) and ethanol (10 ml), and the deposited crystal was filtered to give the title compound (4.98 g; 50%).

Workup

  1. additionAfter the addition, insoluble materials
  2. filtrationwere filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the residue was added ethyl acetate
  5. additionto the resulting solution was added carefully saturated sodium hydrogen carbonate solution
  6. washThe organic phase was washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customAfter removal of the solvent under reduced pressure
  9. customthe residue was crystallized from chloroform (100 ml) and ethanol (10 ml)
  10. filtrationthe deposited crystal was filtered

Sources & evidence

ORD record
ord-034733926c5c42d68486d06769083ccf
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

Loading…