p-Toluenesulfonic acid → Methyl 2-m-tolylbenzo[d]oxazole-7-carboxylate

HRID 415214Notes

Reaction equation

HRID 415214 reaction equation
O[C:2]1[C:11]([NH:12][C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:16]1([CH3:20])[CH:17]=[CH:18][CH:19]=[C:14]([C:13]2[O:21][C:2]3[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=3[N:12]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66620977Methyl 2-hydroxy-3-(3-methylbenzamido)benzoate

Product 1

HCID 66620979Methyl 2-m-tolylbenzo[d]oxazole-7-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 2-hydroxy-3-(3-methylbenzamido)benzoate (1.8 mg, 6.29 mmol) and 4-methylbenzenesulfonic acid (1.61 g, 9.4 mmol) were added to toluene (10 mL) and the mixture was stirred at reflux for 10 hr. The resulting mixture was extracted with ethyl acetate (100 mL×4) and concentrated to obtain methyl 2-m-tolylbenzo[d]oxazole-7-carboxylate as a solid (120 mg, yield 64%). LC-MS (ESI) m/z 269 [M+1]−.

Workup

  1. temperatureat reflux for 10 hr
  2. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-909b4d09b6e147c6a58b24f2f71ff5c4
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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