3-(Trimethoxysilyl)propyl chloride → HCID 86734445, compound

HRID 1415443Notes

Reaction equation

HRID 1415443 reaction equation
ClC[CH2:3][CH2:4][Si:5]([O:10][CH3:11])([O:8][CH3:9])[O:6][CH3:7].[CH2:12]([NH:20][CH3:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH3:22][O-].[Na+]>CO>[CH2:13]([CH:12]([NH:20][CH3:21])[CH2:3][CH2:4][Si:5]([O:10][CH3:11])([O:8][CH3:9])[O:6][CH3:7])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:22]

Participants

5

Reactant 3

HCID 624493-(Trimethoxysilyl)propyl chlorideHCID 75538OctylmethylamineHCID 10942334Sodium Methoxide

Product 1

HCID 86734445HCID 86734445, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 19.9 grams of gamma-chloropropyltrimethoxysilane (commercially available) and 14.3 gm. of octylmethylamine is heated to 100°-120° C. for 16 hours. NMR indicated complete quaternization of the amine. To this mixture is added 0.1 mole of sodium methoxide in 50 ml. of methanol. After stirring for 6 hours the methanol is removed under vacuum and the residue is dissolved in cold hexane and filtered to yield gamma-octylmethylaminopropyltrimethoxysilane. To this product is added 0.1 mole of sodium beta-bromopropionate in 300 ml. of methanol. The mixture is warmed gently for 6 hours, then refluxed for an additional 6 hours to yield the desired quaternary ammonium salt.

Workup

  1. customis removed under vacuum
  2. dissolutionthe residue is dissolved in cold hexane
  3. filtrationfiltered

Sources & evidence

ORD record
ord-075e40b105334c2e8da35b5c7d3d3689
Source dataset
uspto-grants-1977_01
Patent number
US04005118

Reaction notes

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