3,5-Dinitrobenzoyl chloride → HCID 18916073, compound

HRID 1290585Notes

Reaction equation

HRID 1290585 reaction equation
[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[N+:16]([C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([N+:28]([O-:30])=[O:29])[CH:27]=1)[C:22](Cl)=[O:23])([O-:18])=[O:17]>C1(C)C=CC=CC=1>[N+:16]([C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([N+:28]([O-:30])=[O:29])[CH:27]=1)[C:22]([N:7]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]1=[O:8])=[O:23])([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 74323,5-Dinitrobenzoyl chlorideHCID 7768CaprolactamHCID 8471Triethylamine

Product 1

HCID 18916073HCID 18916073, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

All glassware is dried thoroughly, and the reaction is kept under an inert atmosphere (argon) at all times. With stirring, 2.33 g (20.6 mmol) of caprolactam (Aldrich) and 2.30 g (22.7 mmol) of triethylamine (Aldrich, d=0.726 g/mol) are added to 100 mL toluene (Aldrich) in a 3-neck round bottom flask equipped with a reflux condenser, addition funnel, and mechanical stirrer, to give a clear, pale yellow solution. Addition of a solution of 4.75 g (20.6 mmol) of 3,5-dinitrobenzoyl chloride (Aldrich) in 100 mL toluene proceeds dropwise over a period of 30 min. The resulting reaction mixture is heated to reflux and stirred for 16 h. Upon cooling to room temperature, the reaction is filtered to remove the triethylamine hydrochloride, and poured into a separatory funnel. After dilution with 300 mL of chloroform, the organic solution is extracted with 5% aq HCl, 5% aq NaOH, and finally D.I. water. The organic layer is dried over Na2 SO4, filtered, and the solvent removed by evaporation under reduced pressure. Recrystallization of the crude product from toluene followed by drying under vacuum yields N-(3,5-dinitrobenzoyl)caprolactam as a light yellow, crystalline solid.

Workup

  1. customAll glassware is dried thoroughly
  2. customequipped with a reflux condenser, addition funnel, and mechanical stirrer
  3. customto give a clear, pale yellow solution
  4. customThe resulting reaction mixture
  5. temperatureis heated
  6. temperatureto reflux
  7. stirringstirred for 16 h
  8. filtrationthe reaction is filtered
  9. customto remove the triethylamine hydrochloride
  10. additionpoured into a separatory funnel
  11. extractionAfter dilution with 300 mL of chloroform, the organic solution is extracted with 5% aq HCl, 5% aq NaOH
  12. customThe organic layer is dried over Na2 SO4
  13. filtrationfiltered
  14. customthe solvent removed by evaporation under reduced pressure
  15. customRecrystallization of the crude product from toluene
  16. customby drying under vacuum

Sources & evidence

ORD record
ord-d32dde3f685c418bac0549dc84827d04
Source dataset
uspto-grants-1998_05
Patent number
US05753138

Reaction notes

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