Carbon Disulfide → Silane, (3-isothiocyanatopropyl)trimethoxy-

HRID 2103960Notes

Reaction equation

HRID 2103960 reaction equation
[CH3:1][O:2][Si:3]([O:10][CH3:11])([O:8][CH3:9])[CH2:4][CH2:5][CH2:6][NH2:7].[C:12](=S)=[S:13].C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C>O1CCCC1>[N:7]([CH2:6][CH2:5][CH2:4][Si:3]([O:8][CH3:9])([O:10][CH3:11])[O:2][CH3:1])=[C:12]=[S:13]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 83756Aminopropyltrimethoxysilane

Product 1

HCID 9813262Silane, (3-isothiocyanatopropyl)trimethoxy-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In a reaction container mixed were 53.8 g of 3-(trimethoxysilyl)propylamine and 600 ml of dry tetrahydrofuran (THF), with cooling to 0° C. To this solution, 34.2 g of carbon disulfide was added dropwise, and the mixture was stirred at 0° C. for 5 hours in a nitrogen atmosphere. Then, a solution of 61.9 g of dicyclohexyl carbodiimide in 180 ml of dry THF and 3 g of triethylamine were added thereto, and the mixture was allowed to react at 40° C. for 5 hours. THF was removed from the reaction mixture obtained, and the residue was extracted with n-hexane. Then n-hexane was removed from the extract under reduced pressure, and the residue was distilled under reduced pressure, to obtain γ-isothiocyanatopropyltrimethoxysilane.

Workup

  1. additionIn a reaction container mixed
  2. customto react at 40° C. for 5 hours
  3. customTHF was removed from the reaction mixture
  4. customobtained
  5. extractionthe residue was extracted with n-hexane
  6. customThen n-hexane was removed from the
  7. extractionextract under reduced pressure
  8. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-ff43784520554857a70815b01f56c04f
Source dataset
uspto-grants-2009_08
Patent number
US07576167B2

Reaction notes

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