Methanol → HCID 23500293, compound

HRID 1835875Notes

Reaction equation

HRID 1835875 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH2:7].I[CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH:15](O)[CH3:16].C[OH:19]>>[CH2:9]([OH:19])[CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][NH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH2:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 8111DiethylenetriamineHCID 86587426HCID 86587426, compound

Product 1

HCID 23500293HCID 23500293, compoundYield 33%

Procedure

A mixture of diethylene triamine (460 ml, 4.3 mole) and (2-iodoethoxy) ethoxyethanol (7.30 g, 28 mmole) was stirred-at room temperature for 1 hour. The excess of diethylenetriamine was removed by distillation under vacuum. The residue was then treated with aqueous Satd NaOH, extracted with CH2Cl2, dried over MgSO4/Na2CO3, filtered, and concentrated to give a yellow oil. This was purificated by column chromatography on silica with CH3OH/NH40H (10:1), then (5:1) to give 1.43 g (33%) of the title compound as a pale yellow oil. The reaction is shown schematically as follows:

Workup

  1. customThe excess of diethylenetriamine was removed by distillation under vacuum
  2. additionThe residue was then treated with aqueous Satd NaOH
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over MgSO4/Na2CO3
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow oil

Sources & evidence

ORD record
ord-923c697953aa4f33842747924f803586
Source dataset
uspto-grants-2004_08
Patent number
US06774082B2

Reaction notes

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