1-Chloro-2-nitrobenzene → HCID 15869139, compound

HRID 1532648Notes

Reaction equation

HRID 1532648 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.Cl[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]>C(OCC)(=O)C>[N:5]1([CH2:4][CH2:3][CH2:2][NH:1][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

4

Reactant 2

HCID 69451-Chloro-2-nitrobenzeneHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 15869139HCID 15869139, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
125 °C

Procedure

1-(3-Aminopropyl)imidazole (4.55 ml) was added to 2-chloronitrobenzene (3.000 g) and stirred for 15 hours at 125° C. The reaction mixture, with ethyl acetate added thereto, was washed with 1N sodium hydroxide aqueous solution, and extracted with 1N hydrochloric acid aqueous solution. The extract was alkalified with 1N sodium hydroxide aqueous solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate anhydride, and concentrated, thereby yielding the entitled compound (4.442 g) as orange oil.

Workup

  1. washwas washed with 1N sodium hydroxide aqueous solution
  2. extractionextracted with 1N hydrochloric acid aqueous solution
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over sodium sulfate anhydride
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-042275208f064ff69666eda2ccca379c
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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