2-Mercaptoethanol → Ammonia

HRID 1728253Notes

Reaction equation

HRID 1728253 reaction equation
[CH2:1]([CH:3]1[C:7](=[O:8])[CH2:6][C:5]2([CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[O:4]1)[CH3:2].[SH:15][CH2:16][CH2:17]O.[OH-].[Na+]>ClCCl>[NH3:11].[CH2:1]([CH:3]1[C:7]2([O:8][CH2:17][CH2:16][S:15]2)[CH2:6][C:5]2([CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)[O:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 15672-MercaptoethanolHCID 14798Sodium HydroxideHCID 1255222-Ethyl-8-methyl-1-oxa-8-azaspiro[4.5]decan-3-one

Product 2

HCID 222AmmoniaHCID 14852068HCID 14852068, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution (32 ml) of 0.53 g 2-ethyl-8-methyl-1-oxa-8-azaspiro[4,5]decane-3-one in dichloromethane was cooled in ice, 384 μl 2-mercaptoethanol and 2.05 ml boron trifluoride/ether complex were added in that order in an argon atmosphere, and the mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into 23 ml of 20% aqueous solution of caustic soda, stirring was continued for about 15 minutes, and the two separate layers were collected. The aqueous layer was extracted with chloroform, the extract was joined to the organic layer separated above, and the combined solution 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 purified by silica gel column chromatography using, as eluent, a mixed solvent of chloroform/methanol/conc. ammonia (20:1:0.1 by volume), giving 460 mg of 14-ethyl-10-methyl-1,13-dioxa-4-thia-10-aza-dispiro[4,1,5,2]tetradecane as oil. It was then converted to maleate by treatment with maleic acid in isopropanol.

Workup

  1. stirringstirring
  2. waitwas continued for about 15 minutes
  3. customthe two separate layers
  4. customwere collected
  5. extractionThe aqueous layer was extracted with chloroform
  6. customseparated above, and the combined solution
  7. washwas washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationThe dried solution was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9e06f2c35d1c4e2f9738ab807fad36c6
Source dataset
uspto-grants-1994_07
Patent number
USRE034653

Reaction notes

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