Butyl Chloride → N-butyl-4-amino-3,3-dimethylbutyltrimethoxysilane

HRID 1531332Notes

Reaction equation

HRID 1531332 reaction equation
[NH2:1][CH2:2][C:3]([CH3:14])([CH3:13])[CH2:4][CH2:5][Si:6]([O:11][CH3:12])([O:9][CH3:10])[O:7][CH3:8].Cl[CH2:16][CH2:17][CH2:18][CH3:19].C[O-].[Na+]>CO>[CH2:16]([NH:1][CH2:2][C:3]([CH3:14])([CH3:13])[CH2:4][CH2:5][Si:6]([O:11][CH3:12])([O:7][CH3:8])[O:9][CH3:10])[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8005Butyl Chloride2×HCID 10942334Sodium MethoxideHCID 219390334-Amino-3,3-dimethylbutyltrimethoxysilane2×

Product 1

HCID 21253656N-butyl-4-amino-3,3-dimethylbutyltrimethoxysilaneYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
125 °C

Procedure

In a 1 liter 3-necked flask equipped with a magnetic stirrer, heating mantle thermometers and condenser was added 664.1 g (3 moles) of 4-amino-3,3-dimethylbutyltrimethoxysilane and 69.4 g (0.75 mole) of 1-chlorobutane. With stirring, the flask contents were slowly heated to 125° C. and maintained at that temperature for a total of 13 hours. A gas chromatograph of a sample of the flask contents at that point indicated all of the chlorobutane had been consumed in the reaction with the aminofunctional silane. The flask was cooled to room temperature and 162 g of a 25% solution of sodium methoxide in methanol (0.75 mole of sodium methoxide) was added drop-wise by means of an addition funnel. After stirring for 30 minutes the flask contents were pressure filtered and distilled, yielding after removal of methanol and excess 4-amino-3,3-dimethylbutyltrimethoxysilane, 160.7 g of N-butyl-4-amino-3,3-dimethylbutyltrimethoxysilane (bp 90-94° C. at 1 mm Hg, 58% yield). The structure was confirmed by gc-mass spectroscopy and 1H and 13C nmr spectroscopy.

Workup

  1. customIn a 1 liter 3-necked flask equipped with a magnetic stirrer
  2. temperatureheating mantle thermometers and condenser
  3. temperaturemaintained at that temperature for a total of 13 hours
  4. customhad been consumed in the reaction with the aminofunctional silane
  5. temperatureThe flask was cooled to room temperature
  6. stirringAfter stirring for 30 minutes the flask contents
  7. filtrationfiltered
  8. distillationdistilled
  9. customyielding

Sources & evidence

ORD record
ord-63625f56bf4649108ec24eada73f55d2
Source dataset
uspto-grants-2001_03
Patent number
US06197912B1

Reaction notes

Loading…