2-(Methylamino)ethanol → 2-(Benzooxazol-2-yl-methyl-amino)-ethanol

HRID 263982Notes

Reaction equation

HRID 263982 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][NH:12][CH2:13][CH2:14][OH:15]>O1CCCC1>[CH3:11][N:12]([CH2:13][CH2:14][OH:15])[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 119862-Chlorobenzoxazole

Product 1

HCID 102416632-(Benzooxazol-2-yl-methyl-amino)-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-chlorobenzoxazole (15.4 g) in dry tetrahydrofuran (50 ml) was added dropwise to an ice cooled solution of 2-methylaminoethanol (15.0 g) in dry tetrahydrofuran (100 ml) with stirring and protection from atmospheric moisture. The mixture was stirred at 0° C. for 1 hour, allowed to warm to room temperature and stirred for a further 2 hours. The solvent was removed under reduced pressure, the product was dissolved in ethyl acetate (200 ml) and washed with brine (2×150 ml). The organic layer was dried (MgSO4), filtered and the solvent evaporated. Chromatography of the residue on silica-gel in dichloromethane gave the title compound (mp 62°-3° C.) which was used in Preparation 3 without further purification.

Workup

  1. stirringThe mixture was stirred at 0° C. for 1 hour
  2. stirringstirred for a further 2 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe product was dissolved in ethyl acetate (200 ml)
  5. washwashed with brine (2×150 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-f00835aab8d64d05ad4f116b476540a0
Source dataset
uspto-grants-1997_07
Patent number
US05646169

Reaction notes

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