1,2-Ethanedithiol → Ammonia

HRID 1728249Notes

Reaction equation

HRID 1728249 reaction equation
[CH3:1][CH:2]1[C:6](=O)[CH2:5][C:4]2([CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)[O:3]1.[CH2:14]([SH:17])[CH2:15][SH:16].[OH-].[Na+]>ClCCl>[NH3:10].[CH3:13][N:10]1[CH2:11][CH2:12][C:4]2([O:3][CH:2]([CH3:1])[C:6]3([S:17][CH2:14][CH2:15][S:16]3)[CH2:5]2)[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 109021,2-EthanedithiolHCID 14798Sodium HydroxideHCID 101764012,8-Dimethyl-1-oxa-8-azaspiro[4.5]decan-3-one

Product 2

HCID 222AmmoniaHCID 10400364HCID 10400364, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.5 g 2,8-dimethyl-1-oxa-8-azaspiro[4,5]-decan-3-one in 10 ml dichloromethane was cooled in ice, 0.45 ml 1,2-ethanedithiol was added, and 2 ml boron trifluoride/ether complex was then added dropwise while maintaining the temperature below 10° C. After stirring at that temperature for one hour, the reaction mixture was poured into 30 ml of 20% aqueous caustic soda solution. The insoluble matters were filtered off, the filtrate was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The dried solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using, as eluent, a mixed solvent of chloroform/methanol/conc. ammonia (20:1:0.1 by volume), giving 0.46 g of 10,14-dimethyl-13-oxa-1,4-dithia-10-azadispiro[4,1,5,2]tetradecane. It was dissolved in methanol and converted to maleate by addition of an equimolar amount of maleic acid dissolved in the same solvent.

Workup

  1. addition2 ml boron trifluoride/ether complex was then added dropwise
  2. temperaturewhile maintaining the temperature below 10° C
  3. filtrationThe insoluble matters were filtered off
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washthe organic layer was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe dried solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e7a3b59919994cfc9e866458fc8c137f
Source dataset
uspto-grants-1994_07
Patent number
USRE034653

Reaction notes

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