5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrophenyl azide → 5-(2-chloro-4-trifluoromethylphenoxy)benzo-2,1,3-oxadiazole N-oxide

HRID 463598Notes

Reaction equation

HRID 463598 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([N:11]=[N+]=[N-])[CH:10]=1>C1(C)C=CC=CC=1.C1C=CC=CC=1>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]2=[N+:14]([O-:16])[O:15][N:11]=[C:9]2[CH:10]=1

Participants

4

Reactant 1

HCID 135053575-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrophenyl azide

Product 1

HCID 135343365-(2-chloro-4-trifluoromethylphenoxy)benzo-2,1,3-oxadiazole N-oxide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrophenyl azide (1.2 g) is cautiously heated to reflux temperature in toluene (10 ml) and is heated under reflux for 3 hours. The reaction is cooled, and diluted with benzene, washed with water (3X) and with brine, dried, stripped and purified by prep. TLC (6.5% ethyl acetate/hexane) to give 5-(2-chloro-4-trifluoromethylphenoxy)-benzo-2,1,3-oxadiazole N-oxide, m.p. 60°-61°. (C; X=H, Y=Cl, Y'=H, Z=CF3).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe reaction is cooled
  4. washwashed with water (3X) and with brine
  5. customdried
  6. custompurified by prep

Sources & evidence

ORD record
ord-8387a639508c4c748a834c02a612619e
Source dataset
uspto-grants-1985_10
Patent number
US04544400

Reaction notes

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