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

HRID 2119915Notes

Reaction equation

HRID 2119915 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-db537e8a01154cfb895a333ec07db776
Source dataset
uspto-grants-2004_02
Patent number
US06686475B2

Reaction notes

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