Water → HCID 12097381, compound

HRID 989468Notes

Reaction equation

HRID 989468 reaction equation
O.C(=O)([O-])[O-].[K+].[K+].S(O[CH2:13][C:14]([NH2:17])([CH3:16])[CH3:15])(O)(=O)=O.[CH2:18]([SH:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(O)C>[CH3:15][C:14]([NH2:17])([CH3:16])[CH2:13][S:26][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 81441-OctanethiolHCID 11430Potassium CarbonateHCID 2928692-amino-2-methylpropyl hydrogen sulfate

Product 1

HCID 12097381HCID 12097381, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a mixed solvent of 10 ml of water and 10 ml of ethanol was suspended 1.38 g (10 mmol) of potassium carbonate. To the suspension were added 0.85 g (5 mmol) of 2-amino-2-methylpropyl hydrogensulfate and 0.73 g (5 mmol) of 1-octanethiol, and the resulting mixture was gently refluxed for 8 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and the desired compound was extracted three times with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby 1.08 g of 2-methyl-1-n-octylthio-2-propylamine was obtained. The purity was measured in terms of area percentage by gas chromatography and found to be 91%.

Workup

  1. temperaturethe resulting mixture was gently refluxed for 8 hours
  2. customAfter completion of the reaction
  3. extractionthe desired compound was extracted three times with ethyl acetate
  4. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent

Sources & evidence

ORD record
ord-4b50b85bcdb649c2860d9ebdf3a816df
Source dataset
uspto-grants-2003_10
Patent number
US06639109B1

Reaction notes

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