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

HRID 1665629Notes

Reaction equation

HRID 1665629 reaction equation
C1N=CN([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=[O:7])C=1.NC1C=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[OH:23]>CN(C=O)C>[N+:20]([C:18]1[CH:17]=[CH:16][C:15]2[O:23][C:6](=[O:7])[NH:8][C:9]=2[CH:10]=1)([O-:22])=[O:21]

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 434.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

CDI (1.57 g, 19.4 mmol) was added at 0° C. to a stirred solution of 2-amino-4-nitro-phenol (500 mg, 0.6 mmol) in DMF (5 mL) and the resultant was stirred for 30 mins. The mixture was poured onto ice and stirred for 10 minutes. The resulting precipitate was isolated by filtration to afford 470 mg (80%) of 5-nitro-3H-benzooxazol-2-one. 1H NMR: (DMSO-d6): δ 12.4 (b s, 1H), 8.05 (dd, 1H), 7.85 (d, 1H), 7.54 (d, 1H).

Workup

  1. additionThe mixture was poured onto ice
  2. stirringstirred for 10 minutes
  3. customThe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-66cc9ab9580b43b8b5b3e58bb58aee97
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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