Hydrochloric Acid → 5-(5-Chloro-2-benzoxazolyloxy)-2nitrobenzoic acid

HRID 358418Notes

Reaction equation

HRID 358418 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].F[C:19]1[CH:20]=[CH:21][C:22]([N+:28]([O-:30])=[O:29])=[C:23]([CH:27]=1)[C:24]([OH:26])=[O:25].Cl>CS(C)=O.C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([O:10][C:19]3[CH:20]=[CH:21][C:22]([N+:28]([O-:30])=[O:29])=[C:23]([CH:27]=3)[C:24]([OH:26])=[O:25])=[N:7][C:6]=2[CH:11]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 2733Chlorzoxazone2×HCID 11430Potassium CarbonateHCID 27374205-Fluoro-2-nitrobenzoic acid2×

Product 1

HCID 133614775-(5-Chloro-2-benzoxazolyloxy)-2nitrobenzoic acid

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A reactor is charged with 1.69 grams (0.01 mole) of 5-chlorobenzoxazol-2-one (Formula II Compound), 10 milliliters of dimethylsulfoxide, and 2.76 grams (0.02 mole) of anhydrous potassium carbonate. To this mixture is added 1.85 grams (0.01 mole) of 5-fluoro-2-nitrobenzoic acid (Formula III Compound) in 4 milliliters of dimethylsulfoxide. After stirring at about 75° C. to 80° C. for about 18 hours, the reaction mixture is stripped of solvent and the residue is dissolved in a mixture of methylene chloride and water. The mixture is acidified to pH 2 to 3 with 5 normal hydrochloric acid and the aqueous phase is extracted with methylene chloride. The combined organic phases are washed with water and saturated sodium chloride solution. Filtration and removal of solvent affords 5-(5-chloro-2-benzoxazolyloxy)-2nitrobenzoic acid. (Formula IV Compound);

Workup

  1. extractionthe aqueous phase is extracted with methylene chloride
  2. washThe combined organic phases are washed with water and saturated sodium chloride solution
  3. filtrationFiltration and removal of solvent

Sources & evidence

ORD record
ord-6916038da5a34e258a61539118c1da88
Source dataset
uspto-grants-1984_08
Patent number
US04468244

Reaction notes

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