Toluene → HCID 68742154, compound

HRID 1907067Notes

Reaction equation

HRID 1907067 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=O)[CH:3]=[CH:2]1.NCCC[Si:12]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15].C[Si](C)(C)[NH:24][Si](C)(C)C.[C:31]1([CH3:37])C=CC=C[CH:32]=1>[Cl-].[Zn+2].[Cl-]>[CH3:32][CH2:31][CH2:37][CH:20]([O:19][Si:12]([O:13][CH2:14][CH3:15])([O:16][CH2:17][CH3:18])[N:24]1[C:1](=[O:7])[CH:2]=[CH:3][C:4]1=[O:6])[CH3:21]

Participants

6

Reactant 4

HCID 1140Toluene4×HCID 7923Maleic AnhydrideHCID 13521(3-Aminopropyl)triethoxysilaneHCID 13838Hexamethyldisilazane

Product 1

HCID 68742154HCID 68742154, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
80 °C

Procedure

N-(3-propyl triethoxysilyl)maleimide (PSM) is prepared by the addition of 100 mL of a 2.33 molar saturated anhydrous toluene solution of maleic anhydride (22.85 g of anhydride, 0.233 mol) to a one liter flask containing 100 mL of dry toluene and then, under nitrogen, slowly dripping in a solution of 3-aminopropyl triethoxysilane (51.6 g, 54.8 mL, 0.233 mol) dissolved in 100 mL of dry toluene over a 15 minute period. After stirring 2 hours, anhydrous zinc chloride (10 g, 73.3 mmol) and hexamethyldisilazane (HMDS) (47.0 g, 60.7 mL, 0.291 mol) dissolved in 100 mL of dry toluene are added. The solution is heated to 80° C. for 18 hrs with stifling before being filtered and isolated by distillation.

Workup

  1. additionare added
  2. filtrationbefore being filtered
  3. customisolated by distillation

Sources & evidence

ORD record
ord-93b8e064c2eb4a1d8329d4769535f0b9
Source dataset
uspto-grants-2013_12
Patent number
US08597790B2

Reaction notes

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