2-Aminophenol → Ethyl 1,3-benzoxazole-2-carboxylate

HRID 29432Notes

Reaction equation

HRID 29432 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH2:9]([O:11][C:12](OCC)([O:18]CC)[C:13](OCC)=O)[CH3:10]>>[CH2:9]([O:11][C:12]([C:13]1[O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1)=[O:18])[CH3:10]

Participants

3

Reactant 2

HCID 58012-AminophenolHCID 5090273Ethyl 2,2,2-triethoxyacetate

Product 1

HCID 14220914Ethyl 1,3-benzoxazole-2-carboxylateYield 67.5%

Conditions

Temperature
110 °C

Procedure

To 2-aminophenol (437 mg, 4 mmol) was added ethyl triethoxyacetate (3.5 g, 4 eq). The mixture was stirred at 110° C. overnight. The reaction mixture was cooled and triturated with hexane. Filtration gave 516 mg of benzoxazole-2-carboxylic acid ethyl ester as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customtriturated with hexane
  3. filtrationFiltration

Sources & evidence

ORD record
ord-65ea146735684dce99300d1e899b6c38
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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