3,5-Dinitrobenzoyl chloride → HCID 21201139, compound

HRID 1978798Notes

Reaction equation

HRID 1978798 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]1=[O:16].O1CCOCC1.C(N(CC)CC)C.[N+:30]([C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([N+:42]([O-:44])=[O:43])[CH:41]=1)[C:36](Cl)=[O:37])([O-:32])=[O:31]>O>[N+:30]([C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([N+:42]([O-:44])=[O:43])[CH:41]=1)[C:36]([O:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]1=[O:16])=[O:37])([O-:32])=[O:31]

Participants

6

Reactant 4

HCID 74323,5-Dinitrobenzoyl chlorideHCID 8471TriethylamineHCID 312751,4-Dioxane2×HCID 212011151-(2-Hydroxyethyl)-3-phenyl-1H-pyrrole-2,5-dione

Product 1

HCID 21201139HCID 21201139, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 11 three-necked flask equipped with a dropping funnel and a stirring means were placed 11.0 g of N-(2-hydroxyethyl)-a-phenylmaleimide and 500 ml of dioxane, and 7.70 ml of triethylamine was added at 0° C. under stirring. A dioxane solution of 11.5 g of 3,5-dinitrobenzoyl chloride was added dropwise thereto at 0° C. and stirring was continued at room temperature overnight. After completion of the reaction, 11 of water was added to the reaction solution and the resulting crystalline substance was collected by filtration. It was recrystallized twice from ethyl acetate to afford 6.10 g of N-(2-(3,5-dinitrobenzoyl)oxyethyl)-α-phenylmaleimide. This compound was subjected to reduction of a nitro group without any further purification. This compound had a melting point of 179.1-180.7° C.

Workup

  1. customIn a 11 three-necked flask equipped with a dropping funnel
  2. additionwas added at 0° C.
  3. stirringat 0° C. and stirring
  4. additionwas added to the reaction solution
  5. filtrationthe resulting crystalline substance was collected by filtration
  6. customIt was recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-d09f997ab8dd4b2eb0fe9e6b4471f8be
Source dataset
uspto-grants-2001_05
Patent number
US06238752B1

Reaction notes

Loading…