Diethylamine → HCID 20275416, compound

HRID 1578233Notes

Reaction equation

HRID 1578233 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][Si:5]([O:10][CH3:11])([O:8][CH3:9])[O:6][CH3:7].[S:12](Cl)(Cl)(=O)=O.[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18]>CCCCC>[CH2:17]([N:19]([CH2:20][CH3:21])[S:12][S:1][CH2:2][CH2:3][CH2:4][Si:5]([O:10][CH3:11])([O:6][CH3:7])[O:8][CH3:9])[CH3:18]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 20473(3-Mercaptopropyl)trimethoxysilaneHCID 24648Sulfuryl chloride

Product 1

HCID 20275416HCID 20275416, compound

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Procedure

To a 3 liter 3-necked round bottom glass flask fitted with a dry-ice/acetone condenser, stirrer and dropping funnel was charged 196 grams (1.0 moles) 1-mercapto-3-trimethoxysilylpropane and 2 liters of n-pentane. The mixture was stirred until completely homogeneous afterwhich 135 grams (1.0 moles) of sulfuryl chloride was slowly added with stirring at room temperature. Nitrogen was slowly passed through the mixture for about 20 minutes. The liquid contents were transferred to a dropping funnel and slowly added at about 25 C. to a stirred solution of 160 grams (2.19 moles) diethylamine and 0.3 liter n-pentane. After the addition was complete (2 hrs) the mixture was stirred for an additional 0.5 hrs., filtered and the solid residue washed with 0.5 liters n-pentane. The n-pentane solvent was removed under vacuum with nitrogen. Nitrogen was passed through the residue for 16-20 additional hours under atmospheric conditions. The remaining sludge was again filtered to give 204 grams (68 mole % yield) of a liquid product considered to be the desired product. Analysis by GLC indicate 64.13% purity. Elemental analysis based on 64.13% pure C10H25O3NS2Si is: Calc. N, 2.99; S, 13.7. Found N, 3.97; S, 12.9.

Workup

  1. customTo a 3 liter 3-necked round bottom glass flask fitted with a dry-ice/acetone condenser, stirrer
  2. additionwas slowly added
  3. customThe liquid contents were transferred to a dropping funnel
  4. additionslowly added at about 25 C
  5. additionAfter the addition
  6. custom(2 hrs)
  7. stirringwas stirred for an additional 0.5 hrs
  8. filtration, filtered
  9. washthe solid residue washed with 0.5 liters n-pentane
  10. customThe n-pentane solvent was removed under vacuum with nitrogen
  11. filtrationThe remaining sludge was again filtered
  12. customto give
  13. custom204 grams (68 mole % yield) of a liquid product

Sources & evidence

ORD record
ord-a8ef03eb33454fbc8853511019328a09
Source dataset
uspto-grants-1981_09
Patent number
US04292234

Reaction notes

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