p-Toluenesulfonic acid → HCID 18354630, compound

HRID 415186Notes

Reaction equation

HRID 415186 reaction equation
O[C:2]1[C:3]([NH:11][C:12](=[O:22])[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[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+:19]([C:16]1[CH:15]=[CH:14][C:13]([C:12]2[O:22][C:2]3[C:3](=[C:4]([C:5]([OH:7])=[O:6])[CH:8]=[CH:9][CH:10]=3)[N:11]=2)=[CH:18][CH:17]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54244030HCID 54244030, compound

Product 1

HCID 18354630HCID 18354630, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Hydroxy-2-(4-nitrobenzamido)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 at reflux for 17 hr. The solvent was evaporated under reduced pressure and the residue was washed with water (100 mL×3), filtered and dried under reduced pressure at 50° C. to obtain a yellow solid of 2-(4-nitrophenyl)benzo[d]oxazole-4-carboxylic acid (1.42 g, yield 83%). LC-MS (ESI) m/z 285 [M+1]+.

Workup

  1. temperatureat reflux for 17 hr
  2. customThe solvent was evaporated under reduced pressure
  3. washthe residue was washed with water (100 mL×3)
  4. filtrationfiltered
  5. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-2dce9ad8b91441089f568e8f6252b9cb
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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