Ethanethiol → HCID 68470580, compound

HRID 1937433Notes

Reaction equation

HRID 1937433 reaction equation
C(S)C.[H-].[Na+].[H][H].[S:8]([CH2:18][C@@H:19]1[C@@H:25]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:24][C@H:23]2[N:34]([CH3:35])[C@@H:20]1[CH2:21][CH2:22]2)([C:11]1C=CC(C)=C[CH:12]=1)(=O)=O>CN(C)C=O.CCOCC.O>[CH2:11]([S:8][CH2:18][C@@H:19]1[C@@H:25]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:24][C@H:23]2[N:34]([CH3:35])[C@@H:20]1[CH2:21][CH2:22]2)[CH3:12]

Participants

8

Reactant 4

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 70143510HCID 70143510, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68470580HCID 68470580, compoundYield 39.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of ethanethiol (0.5 ml) in dimethylformamide (30 mL) was added sodium hydride (60%, 0.27 g). When the evolution of hydrogen had ceased (1R, 2R, 3S)-2-tosylmethyl-3-(3,4dichlorophenyl)tropane (2.0 g, 4.4 mmol) in dimethylformamide (20 ml) was added. The mixture was stirred at 0° C. for 25 min. The reaction mixture was heated at 100° C. for 5 days. The reaction was cooled to ambient temperature and poured into a mixture of water (500 ml) and ether (100 ml). The phases were separated and the aqueous phase was extracted once more with ether (100 ml). The ether phase was evaporated and the residue was dissolved in ether (75 ml) and washed with water (2×400 ml), dried over MgSO4 and evaporated to dryness. Yield: 1.4 g. of the tite compound. The crude product was purified by column chromatography on silica gel using a mixture of CH2Cl2/MeOH NH3 (aq) (9:1) +1% NH3 (aq). 0.6 g of the title compound was obtained as an oil.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated at 100° C. for 5 days
  3. temperatureThe reaction was cooled to ambient temperature
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted once more with ether (100 ml)
  6. customThe ether phase was evaporated
  7. dissolutionthe residue was dissolved in ether (75 ml)
  8. washwashed with water (2×400 ml)
  9. dry with materialdried over MgSO4
  10. customevaporated to dryness
  11. customThe crude product was purified by column chromatography on silica gel using
  12. additiona mixture of CH2Cl2/MeOH NH3 (aq) (9:1) +1% NH3 (aq)

Sources & evidence

ORD record
ord-01d815a1ec6248d580e6c4d3cdd3fa2e
Source dataset
uspto-grants-2002_05
Patent number
US06395748B2

Reaction notes

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