Nitrogen → Octanethioic acid, S-(3-(triethoxysilyl)propyl) ester

HRID 1793222Notes

Reaction equation

HRID 1793222 reaction equation
N#N.[SH:3][CH2:4][CH2:5][CH2:6][Si:7]([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10].[SiH4].[C:18](Cl)(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CCCCCC.C(N(CC)CC)C>[C:18]([S:3][CH2:4][CH2:5][CH2:6][Si:7]([O:14][CH2:15][CH3:16])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 947NitrogenHCID 8124Octanoyl chlorideHCID 23953SilaneHCID 846581-Propanethiol, 3-(triethoxysilyl)-

Product 1

HCID 12135713Octanethioic acid, S-(3-(triethoxysilyl)propyl) esterYield 87%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8471TriethylamineSolvent

Procedure

Into a 12-liter, three-necked round bottom flask equipped with mechanical stirrer, addition funnel, thermocouple, heating mantle, N2 inlet, and temperature controller were charged 1,021 grams of 3-mercaptopropyltriethoxysilane (SILQUEST® A-1891 silane from OSi Specialties, Inc., a subsidiary of Crompton Corp. of Greenwich, Conn.), 433 grams of triethylamine, and 3,000 ml hexane. The solution was cooled in an ice bath, and 693 grams of octanoyl chloride were added over a two-hour period via the addition funnel. After addition of the acid chloride was complete, the mixture was filtered two times, first through a 0.1:m filter and then through a 0.01:m filter, using a pressure filter, to remove the salt. The solvent was removed under vacuum. The remaining yellow liquid was vacuum distilled to yield 1,349 grams of 3-(octanoylthio)-1-propyltriethoxysilane as a clear, very light yellow liquid. The yield was 87 percent.

Workup

  1. customInto a 12-liter, three-necked round bottom flask equipped with mechanical stirrer, addition funnel
  2. temperatureThe solution was cooled in an ice bath
  3. filtrationthe mixture was filtered two times
  4. filtrationfirst through a 0.1:m filter
  5. filtrationthrough a 0.01:m filter
  6. filtrationfilter
  7. customto remove the salt
  8. customThe solvent was removed under vacuum
  9. distillationdistilled

Sources & evidence

ORD record
ord-8793196be2554b07b1b776d773339178
Source dataset
uspto-grants-2006_07
Patent number
US07078551B2

Reaction notes

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