Ethanolamine → 2-(1,3-Benzoxazol-2-ylamino)ethanol

HRID 257180Notes

Reaction equation

HRID 257180 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.[CH2:11]([CH2:13][NH2:14])[OH:12]>O1CCCC1>[O:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:14][CH2:13][CH2:11][OH:12]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 119862-Chlorobenzoxazole

Product 1

HCID 99898012-(1,3-Benzoxazol-2-ylamino)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-chlorobenzoxazole (12.78 g) in dry tetrahydrofuran (50 ml) was added, over 10 minutes, to a stirred, ice-cooled solution of ethanolamine (15.3 g) in dry tetrahydrofuran (400 ml). The mixture was heated at reflux overnight, cooled, and the solvent evaporated. The residue was partitioned between water (500 ml) and dichloromethane (500 ml), and the resulting white solid filtered off, washed with dichloromethane and dried in vacuo to afford the title compound m.p. 162°-4° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperaturecooled
  4. customthe solvent evaporated
  5. customThe residue was partitioned between water (500 ml) and dichloromethane (500 ml)
  6. filtrationthe resulting white solid filtered off
  7. washwashed with dichloromethane
  8. customdried in vacuo

Sources & evidence

ORD record
ord-137b68512c54435d82af4d2861ea3e31
Source dataset
uspto-grants-1993_11
Patent number
US05260445

Reaction notes

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