Hydrochloric Acid → HCID 21201126, compound

HRID 1978799Notes

Reaction equation

HRID 1978799 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:25]=[C:26]([N+:28]([O-])=O)[CH:27]=1)[C:7]([O:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[CH:15]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]1=[O:24])=[O:8])([O-])=O.Cl.[OH-].[Na+]>O1CCOCC1>[NH2:28][C:26]1[CH:25]=[C:6]([CH:5]=[C:4]([NH2:1])[CH:27]=1)[C:7]([O:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[CH:15]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]1=[O:24])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21201139HCID 21201139, compound

Product 1

HCID 21201126HCID 21201126, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 300 ml three-necked flask equipped with a dropping funnel and a stirring means were placed 8.22 g of N-(2-(3,5-dinitrobenzoyl)oxyethyl)-α-phenylmaleimide and 150 ml of dioxane, and 30.2 g of stannous chloride (dihydrate) was added at room temperature under stirring. Then, 30.2 g of conc. hydrochloric acid was added dropwise thereto, and thereafter, stirring was continued at room temperature for 3 hours. After completion of the reaction, a 2N aqueous solution of sodium hydroxide was added dropwise thereto until it was neutral, and the reaction solution was filtered with Celite. The filtrate was extracted twice with ethyl acetate, and the organic phase was washed three times with water and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the filtrate was concentrated under reduced pressure to afford a yellow solid. This solid was recrystallized twice from ethyl acetate to afford 6.42 g of N-(2-(3,5-diaminobenzoyl)oxyethyl)-α-phenylmaleimide.

Workup

  1. customIn a 300 ml three-necked flask equipped with a dropping funnel
  2. additionwas added at room temperature
  3. stirringstirring
  4. customAfter completion of the reaction
  5. filtrationthe reaction solution was filtered with Celite
  6. extractionThe filtrate was extracted twice with ethyl acetate
  7. washthe organic phase was washed three times with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter the drying agent was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customto afford a yellow solid
  12. customThis solid was recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-5c5ac4e5c4cb4299b8e2e5ac61189103
Source dataset
uspto-grants-2001_05
Patent number
US06238752B1

Reaction notes

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