Hydrochloric Acid → HCID 22723034, compound

HRID 2297707Notes

Reaction equation

HRID 2297707 reaction equation
[ClH:1].C([N:5]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6][CH2:7][SH:8])(=O)C>C(O)(=O)C>[ClH:1].[SH:8][CH2:7][CH2:6][NH:5][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22722828HCID 22722828, compound

Product 1

HCID 22723034HCID 22723034, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Concentrated hydrochloric acid (5 ml) is added to a solution of N-acetyl-N-(2-mercaptoethyl)phenethylamine (500 mg) in acetic acid (5 ml) under a nitrogen atmosphere, and the mixture is refluxed for 24 hours. The reaction mixture is concentrated under reduced pressure, and then a 10% aqueous sodium carbonate solution is added to the concentrate. Weak basicity of the liquid is confirmed, and the whole is extracted with ethyl acetate. The organic layer is washed with saturated brine and dried over anhydrous sodium sulfate. A 4 N solution of hydrogen chloride in ethyl acetate is added to the organic layer, and the mixture is concentrated under reduced pressure. Ether is added to the concentrate, and the resulting precipitate is filtered off to give 244 mg (50%) of the titled compound (Reference compound No. 17-1) as crystals.

Workup

  1. temperaturethe mixture is refluxed for 24 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additiona 10% aqueous sodium carbonate solution is added to the concentrate
  4. extractionthe whole is extracted with ethyl acetate
  5. washThe organic layer is washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. additionA 4 N solution of hydrogen chloride in ethyl acetate is added to the organic layer
  8. concentrationthe mixture is concentrated under reduced pressure
  9. additionEther is added to the concentrate
  10. filtrationthe resulting precipitate is filtered off

Sources & evidence

ORD record
ord-18fe4024d40e4b668131329ed29509bb
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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