Ethylenediaminetetraacetic Acid → 2-Hexyldecylhydroxylamine

HRID 2302130Notes

Reaction equation

HRID 2302130 reaction equation
Cl.[NH2:2][OH:3].[CH2:4]([CH:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:11]Br)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.C(=O)([O-])O.[Na+]>CO>[CH2:4]([CH:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:11][NH:2][OH:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 6049Ethylenediaminetetraacetic AcidHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 18459580Pentadecane, 7-(bromomethyl)-

Product 1

HCID 184595852-Hexyldecylhydroxylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

69 g of hydroxylamine hydrochloride, 30.5 g of 2-hexyldecylbromide, 0.5 g of EDTA and 500 ml of methanol were mixed and thereto 84 g of sodium hydrogencarbonate was added. The resulting mixture was heated under reflux for 3 hours. Then, the reaction mixture was concentrated, ethyl acetate and water were added thereto, the solution obtained was extracted by liquid separation, and the organic phase was dried over magnesium sulfate. The dried organic phase was concentrated and bis(2-hexyldecyl)hydroxylamine as a by-product was removed using silica gel column chromatography to produce the objective compound. The product was a colorless liquid. Yield: 10.5 g (40.9%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThen, the reaction mixture was concentrated
  4. additionethyl acetate and water were added
  5. customthe solution obtained
  6. extractionwas extracted by liquid separation
  7. dry with materialthe organic phase was dried over magnesium sulfate
  8. concentrationThe dried organic phase was concentrated
  9. custombis(2-hexyldecyl)hydroxylamine as a by-product was removed
  10. customto produce the objective compound

Sources & evidence

ORD record
ord-8c40118d0d76464ea61a5bb0a14786b3
Source dataset
uspto-grants-2002_08
Patent number
US06432615B1

Reaction notes

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