1-Chloro-2-nitrobenzene → HCID 19710466, compound

HRID 726161Notes

Reaction equation

HRID 726161 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1Cl)([O-:3])=[O:2].[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 69451-Chloro-2-nitrobenzeneHCID 11430Potassium CarbonateHCID 177271,12-Dodecanediamine

Product 1

HCID 19710466HCID 19710466, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

34 g (0.216 mol) 2-nitro-chlorobenzene and 20 g 1,12-diaminododecane (0.10 mol) are mixed with 40 g potassium carbonate and 200 ml N,N-dimethylformamide (DMF). The mixture is heated with reflux while subjected to a vigorous stirring for four hours. Subsequently, the inorganic salts are filtered off and washed with a small amount of DMF. The entire DMF-phase is distilled under vacuum to remove substantially all DMF. The remanence is cooled, and 200 ml water are added while vigorously stirred. Subsequently, the water phase is decanted off, and the product is caused to crystallize by the addition of approximately 100 ml ethanol. The crystals are filtered off, washed twice with 25 ml ethanol and 100 ml petroleum ether followed by an air-drying of the product. Yield 21.8 g (49%), melting point 79° to 80° C.

Workup

  1. temperatureThe mixture is heated
  2. temperaturewith reflux
  3. filtrationSubsequently, the inorganic salts are filtered off
  4. washwashed with a small amount of DMF
  5. distillationThe entire DMF-phase is distilled under vacuum
  6. customto remove substantially all DMF
  7. temperatureThe remanence is cooled
  8. addition200 ml water are added
  9. stirringwhile vigorously stirred
  10. customSubsequently, the water phase is decanted off
  11. customto crystallize by the addition of approximately 100 ml ethanol
  12. filtrationThe crystals are filtered off
  13. washwashed twice with 25 ml ethanol and 100 ml petroleum ether
  14. customan air-drying of the product

Sources & evidence

ORD record
ord-e17f8b384d264940a1786ca4dae5d6c5
Source dataset
uspto-grants-1998_01
Patent number
US05708123

Reaction notes

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