p-Toluenesulfonic acid → HCID 66621176, compound

HRID 415180Notes

Reaction equation

HRID 415180 reaction equation
O[C:2]1[C:3]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)=[O:13])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:20]([C:16]1[CH:15]=[C:14]([C:12]2[O:13][C:2]3[C:3](=[C:4]([C:5]([OH:7])=[O:6])[CH:8]=[CH:9][CH:10]=3)[N:11]=2)[CH:19]=[CH:18][CH:17]=1)([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66620475HCID 66620475, compound

Product 1

HCID 66621176HCID 66621176, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Hydroxy-2-(3-nitrobenzeneamido)benzoic acid (1.8 g, 6.0 mmol) and 4-methylbenzenesulfonic acid (2 g, 12.0 mmol) were added to toluene (36 mL) and the mixture was stirred under reflux for 10 hr. The solvents was evaporated under reduced pressure and the residue was washed with water (100 mL×3), filtered, the solid was dried in vacuum at 50° C. to obtain 2-(3-nitrophenyl)benzo[d]oxazole-4-carboxylic acid as a yellow solid (1.42 g, yield 83%). LC-MS (ESI) m/z 285 [M+1]+.

Workup

  1. temperatureunder reflux for 10 hr
  2. customThe solvents was evaporated under reduced pressure
  3. washthe residue was washed with water (100 mL×3)
  4. filtrationfiltered
  5. customthe solid was dried in vacuum at 50° C.

Sources & evidence

ORD record
ord-50ad516d35fd460d8113d8c84ed8bfbc
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

Loading…