Ethanethiol → HCID 59948695, compound

HRID 651041Notes

Reaction equation

HRID 651041 reaction equation
[CH2:1]([SH:3])[CH3:2].[H-].[Na+].[CH:6]1([CH2:12][C@H:13]2[CH2:15][O:14]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[NH4+].[Cl-]>CN(C=O)C>[CH:6]1([CH2:12][C@H:13]([OH:14])[CH2:15][S:3][CH2:1][CH3:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59949024HCID 59949024, compound

Product 1

HCID 59948695HCID 59948695, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Ethanethiol (317 μL, 4.3 mmol) was added to a 60% dispersion in mineral oil NaH (180 mg, 4.5 mmol) slurry in DMF (26 mL) at ambient temperature. After stirring for 15 minutes, the product from Example 15C (300 mg, 2.1 mmol) in DMF (2.0 mL) was added to the reaction vessel. After stirring for 30 minutes, a solution of saturated NH4Cl was added to the mixture followed by extraction with EtOAc (2×). The organics were combined, dried (MgSO4), and concentrated. The residue was chromatographed (silica gel; EtOAc/hexanes 1:20) to provide 347 mg (80%) of the title compound as a light yellow oil.

Workup

  1. stirringAfter stirring for 30 minutes
  2. extractionfollowed by extraction with EtOAc (2×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed (silica gel; EtOAc/hexanes 1:20)

Sources & evidence

ORD record
ord-2c4534df552744e6b483ddf708c7c85a
Source dataset
uspto-grants-2001_08
Patent number
US06277871B1

Reaction notes

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