2-Aminophenol → 2-(Chloromethyl)-1,3-benzoxazole

HRID 1030264Notes

Reaction equation

HRID 1030264 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Cl.[Cl:10][CH2:11][C:12](=N)OCC>C(O)C>[Cl:10][CH2:11][C:12]1[O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 58012-AminophenolHCID 12470659Ethyl 2-chloroethanecarboximidate hydrochloride

Product 1

HCID 20619892-(Chloromethyl)-1,3-benzoxazoleYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of o-aminophenol (4.00 g, 36.6 mmol) and ethyl chloroacetimidate hydrochloride (8.68 g, 54.98 mmol) in ethanol (55 mL) was heated at reflux for 18 hours. The reaction mixture was cooled to room temperature and vacuum filtered. The filtrate was concentrated in vacuo, diluted with methylene chloride and filtered again. The methylene chloride filtrate was dried (MgSO4) and concentrated to afford 3.99 g (65%) of product as a brown oil which was used directly in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. filtrationvacuum filtered
  4. concentrationThe filtrate was concentrated in vacuo
  5. additiondiluted with methylene chloride
  6. filtrationfiltered again
  7. dry with materialThe methylene chloride filtrate was dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3e0fa8619f6d43a290051e3fc539557d
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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