Allylamine → N-Allyl-1,1,1-trimethyl-N-(trimethylsilyl)silylamine

HRID 650704Notes

Reaction equation

HRID 650704 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[CH2:10](N)[CH:11]=[CH2:12]>C(C1C=CC=CC=1S(O)(=O)=O)CCCCCCCCCCC>[CH3:1][Si:2]([CH3:9])([CH3:8])[N:3]([CH2:12][CH:11]=[CH2:10])[Si:4]([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 13838Hexamethyldisilazane

Product 1

HCID 82125N-Allyl-1,1,1-trimethyl-N-(trimethylsilyl)silylamineYield 79.4%

Reagents, catalysts & solvents 1

HCID 25457Dodecylbenzenesulphonic acidCatalyst

Procedure

A 500-ml flask equipped with a distillation column, stirrer, thermometer and dropping funnel was charged with 193.7 g (1.2 mol) of hexamethyldisilazane and 7.0 g (0.02 mol) of dodecylbenzenesulfonic acid. To the flask kept at 70° C., 114.2 g (2.0 mol) of allylamine was added over one hour from the dropping funnel. The contents were stirred for 3 hours under reflux. Subsequently, the allylamine was distilled off over 8 hours. From the reaction solution, a fraction of 89 to 90° C. at 40 mmHg was collected by vacuum distillation, yielding 192.0 g of N,N-bis(trimethylsilyl)allylamine.

Workup

  1. customA 500-ml flask equipped with a distillation column, stirrer
  2. customkept at 70° C.
  3. temperatureunder reflux
  4. distillationSubsequently, the allylamine was distilled off over 8 hours
  5. distillationFrom the reaction solution, a fraction of 89 to 90° C. at 40 mmHg was collected by vacuum distillation

Sources & evidence

ORD record
ord-df04e2c4b3fb43b79ada6af63a6acaed
Source dataset
uspto-grants-2001_08
Patent number
US06274754B1

Reaction notes

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