Diethyl Ether → HCID 15895369, compound

HRID 1954674Notes

Reaction equation

HRID 1954674 reaction equation
[CH2:1]([O:3][CH2:4][O:5][C:6]1[CH:23]=[C:22]2[O:24][CH2:25][CH2:26][O:27][C:21]2=[CH:20][C:7]=1[CH2:8][N:9]1C(=O)C2=CC=CC=C2C1=O)[CH3:2].NN.C(OCC)C>C(O)C>[CH2:1]([O:3][CH2:4][O:5][C:6]1[CH:23]=[C:22]2[O:24][CH2:25][CH2:26][O:27][C:21]2=[CH:20][C:7]=1[CH2:8][NH2:9])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9321HydrazineHCID 15895368HCID 15895368, compound

Product 1

HCID 15895369HCID 15895369, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(2-ethoxymethoxy-4,5-ethylenedioxybenzyl)phthalimide (625 mg, 1.69 mmol) was mixed with 0.2 mL (6.4 mmol) hydrazine in 30 mL ethanol and refluxed for three hr. The reaction mixture was cooled, 30 mL ethyl ether was added to the mixture, and a white precipitate was removed by filtration. The filter cake was washed three times with diethyl ether and the combined organic solutions were evaporated to yield a residue that was partitioned between ethyl ether and 10% sodium hydroxide. The organic phase was washed three times with 10% sodium hydroxide, and the aqueous washes were combined and back-extracted twice with dichloromethane. The organic solutions were combined and washed with brine and dried over sodium sulfate/potassium carbonate. Subsequent evaporation of solvent gave 2-ethoxymethoxy-4,5-ethylenedioxybenzylamine as a light yellow oil (346 g, 86% crude), which solidified upon standing. IR: 3375 cm-1.

Workup

  1. temperaturerefluxed for three hr
  2. temperatureThe reaction mixture was cooled
  3. customa white precipitate was removed by filtration
  4. washThe filter cake was washed three times with diethyl ether
  5. customthe combined organic solutions were evaporated
  6. customto yield a residue that
  7. customwas partitioned between ethyl ether and 10% sodium hydroxide
  8. washThe organic phase was washed three times with 10% sodium hydroxide
  9. extractionback-extracted twice with dichloromethane
  10. washwashed with brine
  11. dry with materialdried over sodium sulfate/potassium carbonate
  12. customSubsequent evaporation of solvent

Sources & evidence

ORD record
ord-d798e68745ad45a1bea20b0d89143e67
Source dataset
uspto-grants-2000_09
Patent number
US06124278

Reaction notes

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