Nitrogen → Acetylthiomethyltriethoxysilane

HRID 1793224Notes

Reaction equation

HRID 1793224 reaction equation
[S:1]1[CH:5]=[CH:4]C=[C:2]1C(O)=O.[O-:9]CC.[Na+].N#N.S1C=CC=C1CC(O)=O.ClC[Si:26]([O:33][CH2:34][CH3:35])([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29]>COCCOCCOC>[C:5]([S:1][CH2:2][Si:26]([O:33][CH2:34][CH3:35])([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])(=[O:9])[CH3:4]

Participants

7

Reactant 5

HCID 947NitrogenHCID 107002-Thiophenecarboxylic acidHCID 159702-Thiopheneacetic acidHCID 84858Silane, (chloromethyl)triethoxy-HCID 2723922Sodium ethoxide

Product 1

HCID 12135714AcetylthiomethyltriethoxysilaneYield 55%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
8 °C

Procedure

This example illustrates the preparation of a thiocarboxylate alkoxysilane from a salt of a thiolcarboxylic acid using a nonprotic solvent. 88 grams of powdered sodium ethoxide and 600 ml diglyme were charged into a one-liter, three-neck round-bottomed flask equipped with magnetic stir bar, temperature probe/controller, heating mantle, addition funnel, condenser, N2 inlet, and ice water bath. The solution was cooled to 8° C., and 105 grams of thiolacetic acid was added slowly via the addition funnel, keeping the temperature below 60° C. The solution was allowed to cool to 35° C., and 250 grams of chloromethyltriethoxysilane was added via the addition funnel. After addition was complete, the solution was heated to 70° C., where a brief exotherm to 120° C. was observed. The solution was heated at 70° C. for an additional three hours. A white solid formed which was filtered first through a 0.1:m pressure filter and then a 0.01:m filter to give a clear, black solution. The solvent was removed under reduced pressure, and the remaining liquid vacuum distilled to yield 163 grams of B, as a clear and colorless liquid, (55 percent yield).

Workup

  1. customequipped with magnetic stir bar
  2. temperaturetemperature probe/controller, heating
  3. customthe temperature below 60° C
  4. temperatureto cool to 35° C.
  5. additionAfter addition
  6. temperaturethe solution was heated to 70° C.
  7. customto 120° C.
  8. temperatureThe solution was heated at 70° C. for an additional three hours
  9. customA white solid formed which
  10. filtrationwas filtered first through a 0.1
  11. filtrationm pressure filter
  12. filtrationa 0.01:m filter
  13. customto give a clear, black solution
  14. customThe solvent was removed under reduced pressure
  15. distillationthe remaining liquid vacuum distilled
  16. customto yield 163 grams of B

Sources & evidence

ORD record
ord-e50976b1d03a405c8b69ff3c747f0580
Source dataset
uspto-grants-2006_07
Patent number
US07078551B2

Reaction notes

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