Diethylamine → Isobutyl(diethylamino)dimethoxysilane

HRID 1953176Notes

Reaction equation

HRID 1953176 reaction equation
C([Mg]Cl)(C)C.[CH2:6]([NH:8][CH2:9][CH3:10])[CH3:7].[CH2:11]([Si:15](OC)([O:18][CH3:19])[O:16][CH3:17])[CH:12]([CH3:14])[CH3:13]>O1CCCC1>[CH2:11]([Si:15]([N:8]([CH2:9][CH3:10])[CH2:6][CH3:7])([O:18][CH3:19])[O:16][CH3:17])[CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8021Diethylamine2×HCID 87622IsobutyltrimethoxysilaneHCID 178418918HCID 178418918, compound

Product 1

HCID 23303878Isobutyl(diethylamino)dimethoxysilaneYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
42.5 °C

Procedure

Following the same general procedure described in Example 1, a flask was charged with one mol of isopropylmagnesium chloride in 500 ml of tetrahydrofuran under a dry nitrogen atmosphere and stirred. To this was added 1.05 mol (76.8 g) of diethylamine over a period of one hour. During the addition of the diethylamine to the reaction mixture, the pot temperature was maintained at 40-45° C. After the addition was complete, the reaction mixture was refluxed for 30 minutes to complete the evolution of the gas. The reaction mixture was cooled to a pot temperature of 50° C. and one mol (178 g) of isobutyltrimethoxysilane was added over a period of one hour. The reaction mixture was refluxed at a pot temperature of 75° C. for four hours to complete the reaction. The isobutyl(diethylamino)dimethoxysilane was filtered under a nitrogen atmosphere from the magnesium methoxychloride salt. The salt cake was washed with ether (2×200 ml) to obtain the residual isobutyl(diethylamino)dimethoxysilane. The combined filtrate was distilled to a pot temperature of 100° C. to remove the lighter fraction and the residue distilled under reduced pressure to yield 153 g of isobutyl(diethylamino)dimethoxysilaie as a colorless oil (purity>98%); bp 104° C./30 mm. The total yield was 79% of theoretical.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was refluxed for 30 minutes
  3. additionwas added over a period of one hour
  4. temperatureThe reaction mixture was refluxed at a pot temperature of 75° C. for four hours
  5. customthe reaction
  6. filtrationThe isobutyl(diethylamino)dimethoxysilane was filtered under a nitrogen atmosphere from the magnesium methoxychloride salt
  7. washThe salt cake was washed with ether (2×200 ml)

Sources & evidence

ORD record
ord-854b7a241c5f4930ae9a284f5dfc22e9
Source dataset
uspto-grants-2000_09
Patent number
US06114558

Reaction notes

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