Dimethylcarbamoyl Chloride → HCID 20227442, compound

HRID 926408Notes

Reaction equation

HRID 926408 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].C(N(CC)CC)C.[NH2:14][CH2:15][CH2:16][CH2:17][Si:18]([O:23][CH3:24])([O:21][CH3:22])[O:19][CH3:20]>O1CCOCC1>[CH3:1][N:2]([CH3:6])[C:3]([NH:14][CH2:15][CH2:16][CH2:17][Si:18]([O:23][CH3:24])([O:19][CH3:20])[O:21][CH3:22])=[O:4]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 83756Aminopropyltrimethoxysilane

Product 1

HCID 20227442HCID 20227442, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

5.0 g (46.5 mmol) N,N-dimethylcarbamoyl chloride (Sigma-Aldrich, Switzerland) and 40 mL dried dioxane (Sigma-Aldrich, Switzerland) were added to a 250-mL round-bottom two-neck flask equipped with a reflux cooler. 4.71 g (46.5 mmol) triethylamine (Sigma-Aldrich, Switzerland) and 8.34 g (46.5 mmol) 3-aminopropyltrimethoxysilane (Silquest A-1110, Momentive Performance Materials Inc., USA) were added dropwise under nitrogen, with stirring. After the exothermic reaction subsided, the resulting whitish suspension was stirred at 90° C. for 3 hours. A gradual color change to orange was observed. After cooling to 50° C., the solid was separated by double filtration, and the solvent was removed at 60° C. for 1 hour on a rotary evaporator. 9.6 g of the desired silane was obtained as a brown liquid. The silane was designated as DMA1100 and used without further purification.

Workup

  1. customequipped with a reflux cooler
  2. customAfter the exothermic reaction
  3. stirringthe resulting whitish suspension was stirred at 90° C. for 3 hours
  4. customthe solid was separated by double filtration
  5. customthe solvent was removed at 60° C. for 1 hour on a rotary evaporator

Sources & evidence

ORD record
ord-c2c7882687f04198b3b48bf9724258ff
Source dataset
uspto-grants-2016_03
Patent number
US09284447B2

Reaction notes

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