Formaldehyde → HCID 207656, compound

HRID 1386042Notes

Reaction equation

HRID 1386042 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[N+:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=[O:18])[CH3:17])([O-:9])=[O:8].C=O.[C:21](=O)([O-])[O-].[Na+].[Na+]>C(O)C>[O:4]1[CH2:5][CH2:6][N:1]([CH2:21][CH2:17][C:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N+:7]([O-:9])=[O:8])=[O:18])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8083MorpholineHCID 10340Sodium CarbonateHCID 113462'-Nitroacetophenone

Product 1

HCID 207656HCID 207656, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of morpholine (2.27 g, 0.026 mol) in ethanol (10 ml) was treated with c-HCl (3 ml) for 10 mins, concentrated under reduced pressure to prepare morpholine HCl salt. To this mixture, 2′-nitroacetophenone (3.3 g, 0.02 mol), paraformaldehyde (0.8 g, 0.029 mol), c-HCl (0.1 ml) and anhydrous ethanol (10 ml) were added. The reaction mixture was stirred under reflux for 30 hrs. This reaction mixture was then cooled to room temperature, alkalized with 10% sodium carbonate solution, and the reaction mixture was extracted with dichloromethane(3×50 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by flash column chromatography with 5% ethanol in dichloromethane to give the desired product (1.5 g, 35%) as an oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto prepare morpholine HCl salt
  3. temperatureunder reflux for 30 hrs
  4. extractionthe reaction mixture was extracted with dichloromethane(3×50 ml)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product
  8. customThe crude product was purified by flash column chromatography with 5% ethanol in dichloromethane

Sources & evidence

ORD record
ord-6bcb3e66e844470aa93fe8ce6f67d9d2
Source dataset
uspto-grants-2001_07
Patent number
US06265413B1

Reaction notes

Loading…