Hydroxide → 2-Aminobenzoxazole

HRID 1295825Notes

Reaction equation

HRID 1295825 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(OCC)(=O)C.[N:15]#[C:16]Br.[OH-]>O>[NH2:15][C:16]1[O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 961HydroxideHCID 58012-AminophenolHCID 8857Ethyl AcetateHCID 10476Cyanogen Bromide

Product 1

HCID 207072-AminobenzoxazoleYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 2.5 g 2-aminophenol (6-1) and 20 ml ethyl acetate was heated to 45° C. 3 g of cyanogen bromide was added to the mixture. The mixture was stirred at 45-50° C. for 12 hours. After cooling to room temperature, 1.5 g of podium hydroxide in 15 ml of water was added. The organic layer was separated and washed with brine until neutral pH. Toluene (5 ml) was added and the solvent was removed to yield 2.71 g (88%) 2-aminobenzoxazol (6-2).

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe organic layer was separated
  3. washwashed with brine until neutral pH
  4. additionToluene (5 ml) was added
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-5ac0244f5c32463d87be6b25aa31d312
Source dataset
uspto-grants-2007_07
Patent number
US07244752B2

Reaction notes

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