Formaldehyde → 3-Phenyloxazolidine

HRID 2251737Notes

Reaction equation

HRID 2251737 reaction equation
[C:1]1([NH:7][CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]=O>CO>[C:1]1([N:7]2[CH2:8][CH2:9][O:10][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 31235N-(2-Hydroxyethyl)aniline2×

Product 1

HCID 5197873-Phenyloxazolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3POX A 500 mL 3-neck flask was equipped with a magnetic stirrer, a reflux condenser, an addition funnel, and a heating mantle with power supply. The flask was charged with 137.17 g (1.0 mole) of N-phenylethanolamine (NPEA) and 25 g of methanol. The addition funnel was charged with 55.20 g of Formcel® (1.01 moles of formaldehyde). The NPEA solution was stirred at room temperature under a blanket of nitrogen, and the Formcel® was added over a period of 1.25 hours. After completing the addition, the reaction mixture was stirred at room temperature overnight. The bulk of the solvent was removed from the reaction mixture by rotary evaporation. Toluene was added to remove water as an azeotrope. The yield of 3POX was 144.54 g (97%) as a clear, amber oil. Product structure was confirmed by NMR and GC/MS analyses.

Workup

  1. custom3POX A 500 mL 3-neck flask was equipped with a magnetic stirrer, a reflux condenser, an addition funnel
  2. additionthe Formcel® was added over a period of 1.25 hours
  3. additionthe addition
  4. customThe bulk of the solvent was removed from the reaction mixture by rotary evaporation
  5. additionToluene was added
  6. customto remove water as an azeotrope

Sources & evidence

ORD record
ord-1acbc0f8663b406485a8f12e6d3f3c29
Source dataset
uspto-grants-2008_01
Patent number
US07319131B2

Reaction notes

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