Tetrahydrofuran → 4 - nitro - 2(3H) - benzoxazolone

HRID 1505176Notes

Reaction equation

HRID 1505176 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].C1C[O:15][CH2:14]C1>CCOC(C)=O>[N+:8]([C:7]1[C:2]2[NH:1][C:14](=[O:15])[O:11][C:3]=2[CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 159339584 - nitro - 2(3H) - benzoxazoloneYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To 2-amino-3-nitrophenol 3b (2 g, 13.00 mmol) dissolved in THF (50 ml) was added in one portion DCI (1.5 equiv., 19.6 mmol, 3.176 g) and the reaction was refluxed for 4 hours. (TLC AcOEt 1/petroleum ether 1). The reaction was evaporated and the crude material was dissolved in HCL 2N and extracted 3 times with chloroform. The combined organic phases were washed with water, brine, dried over sodium sulfate and concentrated under vacuum. The crude solid was crystallized from ether giving 1.5 g of a beige solid. Yield=65% 1HNMR (DMSO, 200 MHz) δ 7.27 (1H, t, J=7.8 Hz), 7.72 (1H, dd, J=8.2 Hz, J′=1 Hz), 7.93 (1H, dd, J=8.4 Hz, J′=0.6 Hz), 12.64 (1H, bs)

Workup

  1. additionwas added in one portion DCI (1.5 equiv., 19.6 mmol, 3.176 g)
  2. temperaturethe reaction was refluxed for 4 hours
  3. customThe reaction was evaporated
  4. dissolutionthe crude material was dissolved in HCL 2N
  5. extractionextracted 3 times with chloroform
  6. washThe combined organic phases were washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe crude solid was crystallized from ether giving 1.5 g of a beige solid

Sources & evidence

ORD record
ord-2c726acd12e040cd9262c97d9ba2ab8c
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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