Hydrochloric Acid → HCID 21201126, compound

HRID 2288946Notes

Reaction equation

HRID 2288946 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

A three neck flask of 300 ml equipped with a dropping funnel and a stirrer was charged with 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 thereto while stirring at a room temperature. Dropwise added thereto was 30.2 g of conc. hydrochloric acid at 10° C., and after adding, the mixture was stirred at a room temperature for 3 hours. After finishing the reaction, a 2 N sodium hydroxide aqueous solution was dropwise added to neutralization to filter the reaction solution with cerite. The filtrate was extracted with ethyl acetate twice, and the organic phase was washed with water three times. Then, it was dried on magnesium sulfate anhydrous. After filtering the desiccating agent off, the solution was concentrated under reduced pressure to obtain a yellow solid material. This was recrystallized in ethyl acetate twice to obtain 6.42 g of N-(2-(3,5-diaminobenzoyl)oxyethyl)-α-phenylmaleimide. This compound had a melting point and an NMR spectrum shown below:

Workup

  1. customA three neck flask of 300 ml equipped with a dropping funnel and a stirrer
  2. additionwas added
  3. additionDropwise added
  4. customat 10° C.
  5. additionafter adding
  6. stirringthe mixture was stirred at a room temperature for 3 hours
  7. customthe reaction
  8. filtrationto filter the reaction solution with cerite
  9. extractionThe filtrate was extracted with ethyl acetate twice
  10. washthe organic phase was washed with water three times
  11. customThen, it was dried on magnesium sulfate anhydrous
  12. filtrationAfter filtering the desiccating agent off, the solution
  13. concentrationwas concentrated under reduced pressure
  14. customto obtain a yellow solid material
  15. customThis was recrystallized in ethyl acetate twice

Sources & evidence

ORD record
ord-c046472223e14da49098665d69b45f86
Source dataset
uspto-grants-2000_07
Patent number
US06090909

Reaction notes

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