Ethanethiol → HCID 54717659, compound

HRID 1828646Notes

Reaction equation

HRID 1828646 reaction equation
C(S)C.[H-].[Na+].[CH2:6]([O:10][C:11]([C:13]1[S:17][C:16]2[CH:18]=[C:19]([O:24]C)[C:20]([O:22][CH3:23])=[CH:21][C:15]=2[C:14]=1[OH:26])=[O:12])[CH2:7][CH2:8][CH3:9].[NH4+].[Cl-]>CN(C=O)C>[CH2:6]([O:10][C:11]([C:13]1[S:17][C:16]2[CH:18]=[C:19]([OH:24])[C:20]([O:22][CH3:23])=[CH:21][C:15]=2[C:14]=1[OH:26])=[O:12])[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 54717657HCID 54717657, compound

Product 1

HCID 54717659HCID 54717659, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.45 ml (60 mmol) ethanethiol and 2.62 g (60 mmol, 60%) NaH were stirred for 15 mins. at room temperature in 100 ml DMF. 9.31 g (30 mmol) XIII were added to the resulting solution, followed by refluxing for 4 h. After hydrolysis with 25 ml saturated NH4Cl solution, the solvents were removed in vacuo, the residue was taken up in 500 ml ethyl acetate and washed with water. After drying over Na2SO4, flash chromatography (250 g SiO2, n-hexane:ethyl acetate=2:1+1% acetic acid), pre-adsorption: 25 g SiO2/CHCl3) yielded 6.89 g (23 mmol, 78%) XVI.

Workup

  1. customat room temperature
  2. temperatureby refluxing for 4 h
  3. customthe solvents were removed in vacuo
  4. washwashed with water
  5. dry with materialAfter drying over Na2SO4, flash chromatography (250 g SiO2, n-hexane:ethyl acetate=2:1+1% acetic acid)

Sources & evidence

ORD record
ord-77a7a79c392c45c4be84583dede5eb6a
Source dataset
uspto-grants-2006_06
Patent number
US07060109B2

Reaction notes

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