Hydrochloric Acid → N~1~,N~3~-Bis(4,5-dichloro-2-nitrophenyl)propanediamide

HRID 1154627Notes

Reaction equation

HRID 1154627 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13](Cl)(=[O:18])[CH2:14][C:15](Cl)=[O:16].[ClH:20]>C1COCC1>[Cl:9][C:5]1[C:6]([Cl:8])=[CH:7][C:2]([NH:1][C:13](=[O:18])[CH2:14][C:15]([NH:1][C:2]2[CH:7]=[C:6]([Cl:20])[C:5]([Cl:9])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])=[O:16])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 74269Propanedioyl dichlorideHCID 811494,5-Dichloro-2-nitroaniline

Product 1

HCID 20434172N~1~,N~3~-Bis(4,5-dichloro-2-nitrophenyl)propanediamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Amino-4,5-dichloro-2-nitrobenzene (113.84 g, 0.55 moles) was dissolved in THF (500 ml). Malonyl chloride (38.75 g, 0.27 moles) was added to the mixture heated to reflux. Another 500 ml portion of THF was added and refluxing was continued for two hours. HCl evolved during the reaction. The reaction mixture was then chilled in an ice bath, the solid was filtered off, washed with cold THF, and dried. A second yield was obtained by concentrating the filtrate, filtering off the solid, making a slurry of the solid in diethyl ether and filtering again. Yield 166.8 g (88%). Product was used as isolated for the next step in the sequence. Anal. Calcd. for C15H8Cl4N4O6 : C, 37.4; H, 1.7; Cl, 29.4; N, 11.6. Found: C, 37.4; H, 1.3; Cl, 29.4; N, 11.6

Workup

  1. temperatureheated to reflux
  2. temperaturerefluxing
  3. temperatureThe reaction mixture was then chilled in an ice bath
  4. filtrationthe solid was filtered off
  5. washwashed with cold THF
  6. customdried
  7. customA second yield
  8. customwas obtained
  9. concentrationby concentrating the filtrate
  10. filtrationfiltering off the solid
  11. filtrationfiltering again
  12. customas isolated for the next step in the sequence

Sources & evidence

ORD record
ord-86603f18e82b4fb4ab13bb500cad59cc
Source dataset
uspto-grants-1984_12
Patent number
US04490463

Reaction notes

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