1,1'-Carbonyldiimidazole → 5-Nitro-2,3-dihydro-1,3-benzoxazol-2-one

HRID 2280343Notes

Reaction equation

HRID 2280343 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].C1N=CN([C:17](N2C=NC=C2)=[O:18])C=1>C1COCC1>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:11][C:17](=[O:18])[NH:1][C:2]=2[CH:7]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 2639655-Nitro-2,3-dihydro-1,3-benzoxazol-2-oneYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 2-amino-4-nitrophenol (5 g, 32.44 mmol) and CDI (6.3 g, 38.93 mmol) in THF (60 mL) was heated at refluxing for 16 h. Cooled to room temperature, the solvent was removed under reduced pressure, the residue was dissolved in DCM (100 mL) and poured into 2N HCl solution (200 mL) with stirring, after 30 min, collected the solid and washed with water (50 mL×2), dried in vacuo to get compound 39-1 as a yellow solid (5.1 g, yield 87%).

Workup

  1. temperaturewas heated
  2. temperatureat refluxing for 16 h
  3. customthe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in DCM (100 mL)
  5. additionpoured into 2N HCl solution (200 mL)
  6. customcollected the solid
  7. washwashed with water (50 mL×2)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-d652cc53ca6140f2a13d3d3888c37f26
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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