Water → Bis-(2-methylthioethyl)-amine

HRID 2296588Notes

Reaction equation

HRID 2296588 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][NH:5][C:6](=O)[CH2:7][S:8][CH3:9].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:1][S:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][CH3:9]

Participants

5

Reactant 3

HCID 962Water2×HCID 18387078S-methyl-thioglycolic Acid-N-(2-methylthioethyl)-amideHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 15410127Bis-(2-methylthioethyl)-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.18 g of S-methyl-thioglycolic acid-N-(2-methylthioethyl)-amide (Example 8a) is dissolved in 350 ml of tetrahydrofuran and added in drops to a suspension of 5.48 g of lithium aluminum hydride in 350 ml of tetrahydrofuran under a cover-gas atmosphere. Then, it is refluxed for 18 hours. While being cooled in an ice bath, the excess lithium aluminum hydride is carefully hydrolyzed by adding 100 ml of water in drops, it is stirred for 1 more hour, and then another 700 ml of water is added. The solution is extracted three times with methylene chloride/methanol 10/1, and the combined organic phases are washed with water one time. After concentration by evaporation, the residue is purified by chromatography with the mobile solvent system of methylene chloride/methanol: yield 1.5 g=32% of theory.

Workup

  1. temperatureThen, it is refluxed for 18 hours
  2. temperatureWhile being cooled in an ice bath
  3. extractionThe solution is extracted three times with methylene chloride/methanol 10/1
  4. washthe combined organic phases are washed with water one time
  5. concentrationAfter concentration
  6. customby evaporation
  7. customthe residue is purified by chromatography with the mobile solvent system of methylene chloride/methanol

Sources & evidence

ORD record
ord-5f6d9bdee2f34b24a6703df1c0c635ab
Source dataset
uspto-grants-2002_12
Patent number
US06488909B1

Reaction notes

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