Formaldehyde → Benzoxazines

HRID 2110544Notes

Reaction equation

HRID 2110544 reaction equation
[C:1]([NH2:5])(C)(C)C.C=[O:7].O.[C:9]1([CH3:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[O:7]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:15]=[CH:1][NH:5]1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 1140TolueneHCID 6385Tert-Butylamine

Product 1

HCID 17845026BenzoxazinesYield 78%

Procedure

A 500 mL three-neck round-bottom flask with a stir-bar was charged with tert-butylamine (14.6 g, 200 mmole), paraformaldehyde (15.0 g, 500 mmole), siloxane-bridged-bisphenol (26.8 g, 0.1 mol, prepared by the procedure described in Example 10), and toluene (200 mL) were placed into a 500 mL. The flask was connected to a Dean-Stark trap and condenser and the reaction mixture was heated to reflux for 4.0 hours while stirring. A total of 7.2 ml (400 mmol) of water was collected. The reaction mixture was allowed to cool to room temperature and passed through a thin layer of silica gel. The toluene was removed by rotary evaporation and the residue was sparged with nitrogen gas for five hours at 60° C. The final product was a fairly mobile, clear, red liquid. The yield was 78% of theory.

Workup

  1. customprepared by the procedure
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 4.0 hours
  4. customThe toluene was removed by rotary evaporation
  5. customthe residue was sparged with nitrogen gas for five hours at 60° C

Sources & evidence

ORD record
ord-34edbe191a764df480fb7e8a0ee5b209
Source dataset
uspto-grants-2009_04
Patent number
US07517925B2

Reaction notes

Loading…