4-Hydroxybenzaldehyde → 4-[2-(N-Methyl-N-(2-benzoxazolyl)amino)ethoxy]benzaldehyde

HRID 359719Notes

Reaction equation

HRID 359719 reaction equation
[CH3:1][N:2]([CH2:12][CH2:13][OH:14])[C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:35]1[CH:42]=[CH:41][C:38]([CH:39]=[O:40])=[CH:37][CH:36]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][N:2]([CH2:12][CH2:13][O:14][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=[O:40])=[CH:37][CH:36]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 102416632-(Benzooxazol-2-yl-methyl-amino)-ethanol

Product 1

HCID 100402134-[2-(N-Methyl-N-(2-benzoxazolyl)amino)ethoxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solutiOn of 2-[N-methyl-N-(2-benzoxazolyl) amino]ethanol (9.6 g), triphenylphosphine (13.1 g) and 4-hydroxybenzaldehyde (6.1 g) in dry tetrahydrofuran (150 ml) was added dropwise a solution of diethyl azodicarboxylate (9.0 g) in dry tetrahydrofuran (30 ml), under a blanket of nitrogen with stirring at room temperature. The solution was stirred overnight at room temperature following which the solvent was removed under reduced pressure. The residue was dissolved in diethyl ether (300 ml), filtered and the ether solution was washed with dilute sodium hydroxide solution (200 ml), saturated brine (200 ml), dried (MgSO4), filtered and the solvent evaporated. The title compound (mp 97°-98° C.) was obtained after chromatography on silica-gel, eluting with dichloromethane. 1H NMR δ (CDCl3) 3 30 (3H, s); 3.85 (2H, t); 4.30 (2H, t) 6.80-7.85 (8H, complex); 9.85 (1H, s).

Workup

  1. stirringThe solution was stirred overnight at room temperature
  2. customwas removed under reduced pressure
  3. dissolutionThe residue was dissolved in diethyl ether (300 ml)
  4. filtrationfiltered
  5. washthe ether solution was washed with dilute sodium hydroxide solution (200 ml), saturated brine (200 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-25643cc84cf149c3bb86d2902d2a3d44
Source dataset
uspto-grants-1991_03
Patent number
US05002953

Reaction notes

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