Acetic Acid → 2(3h)-benzoxazolone, 5-chloro-6-nitro-

HRID 1058213Notes

Reaction equation

HRID 1058213 reaction equation
[CH:1]1[C:6]([Cl:7])=[CH:5][C:4]2[NH:8][C:9]([O:11][C:3]=2[CH:2]=1)=[O:10].C(O)(=O)C.[N+:16]([O-])([OH:18])=[O:17]>N([O-])=O.[Na+].O>[Cl:7][C:6]1[C:1]([N+:16]([O-:18])=[O:17])=[CH:2][C:3]2[O:11][C:9](=[O:10])[NH:8][C:4]=2[CH:5]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 2733Chlorzoxazone

Product 1

HCID 2415982(3h)-benzoxazolone, 5-chloro-6-nitro-Yield 87%

Reagents, catalysts & solvents 2

HCID 23668193Sodium NitriteCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

In a 250-ml flask, place 17.0 g (0.1 m) of chlorzoxazone (1b; X=Cl), 50 ml of acetic acid, and 0.14 g of sodium nitrite. Warm and stir the slurry to 50° C. Add 11.3 g (0.125 m) of concentrated nitric acid (70%) and stir the mixture at 55°-63° C. for 5 hrs. Add 100 ml of hot water, cool to room temperature and let it stand overnight. Collect solid, wash with water, and dry in air to give 18.7 g (87%) of 5-chloro-6-nitro-benzoxazol-2-one (2b; X=Cl) as pale yellow solids.

Workup

  1. temperatureWarm
  2. stirringstir the mixture at 55°-63° C. for 5 hrs
  3. temperaturecool to room temperature
  4. customCollect solid
  5. washwash with water
  6. customdry in air

Sources & evidence

ORD record
ord-cc3e72dfcc034f048d8f3ca65a4ec15d
Source dataset
uspto-grants-2003_02
Patent number
US06515176B1

Reaction notes

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