Sodium Hydroxide → HCID 69930958, compound

HRID 2297706Notes

Reaction equation

HRID 2297706 reaction equation
C1(C)C=CC=CC=1.[H-].[Li+].COCCO[Al+]OCCOC.[H-].[CH2:22]([S:29][CH:30]([CH2:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH:31]([CH2:37][S:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[NH:32]S(C)(=O)=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:22]([S:29][CH:30]([CH2:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)[CH:31]([CH2:37][S:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[NH2:32])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 69930733HCID 69930733, compoundHCID 69931214HCID 69931214, compound

Product 1

HCID 69930958HCID 69930958, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 65% bis(2-methoxyethoxy)aluminum lithium hydride toluene solution (3.3 ml) is added to a solution of 2-(benzylthio)-1-[(benzylthio)methyl]-N-mesyl-N-(phenethyl)ethylamine (1.34 g) obtained in 2) in anhydrous toluene (5 ml) under a nitrogen atmosphere, and the mixture is refluxed overnight. A 2 N aqueous sodium hydroxide solution is added to the reaction mixture under ice cooling, and the whole is extracted with ether. The organic layer is washed with a 2 N aqueous sodium hydroxide solution, water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography to give 0.80 g (71%) of the titled compound (Reference compound No. 16-1).

Workup

  1. temperaturethe mixture is refluxed overnight
  2. extractionthe whole is extracted with ether
  3. washThe organic layer is washed with a 2 N aqueous sodium hydroxide solution, water and saturated brine successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9f31789870b3403399d565430c9082e2
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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