1,7-Tetrasiloxanediol, 1,1,3,3,5,5,7,7-octamethyl- → N-Methylacetamide

HRID 850685Notes

Reaction equation

HRID 850685 reaction equation
O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](O)(C)C.[CH2:18]([O:20][Si:21]([O:32][CH2:33][CH3:34])([O:29][CH2:30][CH3:31])[CH:22]([N:24]([CH3:28])[C:25](=[O:27])[CH3:26])[CH3:23])[CH3:19]>C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C(O)C>[CH3:22][NH:24][C:25](=[O:27])[CH3:26].[CH2:30]([O:29][Si:21]([O:32][CH2:33][CH3:34])([O:20][CH2:18][CH3:19])[CH:22]([N:24]([CH3:28])[C:25](=[O:27])[CH3:26])[CH3:23])[CH3:31]

Participants

6

Reactant 2

HCID 765041,7-Tetrasiloxanediol, 1,1,3,3,5,5,7,7-octamethyl-HCID 11043619HCID 11043619, compound

Product 2

HCID 6582N-MethylacetamideHCID 11043619HCID 11043619, compound

Reagents, catalysts & solvents 2

HCID 11192Zinc AcetateCatalystHCID 702EthanolSolvent

Procedure

2 g of 1,7-dihydroxy-1,1,3,3,5,5,7,7-octamethyltetrasiloxane were mixed with 3.5 g of N-1-(triethoxysilyl)ethyl-N-methylacetamide, in which 20 mg of zinc acetate had been dissolved. The reaction was followed with the aid of 29Si NMR spectroscopy. After a reaction time of 24 hours at room temperature, the OH groups had reacted quantitatively. The end groups formed were exclusively the desired 1-(N-methylacetamido)ethyldiethoxysiloxy groups. Ethoxydimethylsiloxy groups, which could have formed through reaction of the OH groups with ethanol, were not observed. Triethoxysiloxy end groups, which could have been produced by elimination of N-methylacetamide from the N-1-(triethoxysilyl)ethyl-N-methylacetamide used, were likewise not detectable.

Workup

  1. dissolutionhad been dissolved
  2. customAfter a reaction time of 24 hours at room temperature, the OH groups had reacted quantitatively
  3. customThe end groups formed

Sources & evidence

ORD record
ord-4c861bb70f4641229eb237be54eaedbd
Source dataset
uspto-grants-2000_01
Patent number
US06018011

Reaction notes

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