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

HRID 415214

Reaktionsgleichung

Reaktionsgleichung von HRID 415214
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

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 66620977HCID 66620977, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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]−.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-909b4d09b6e147c6a58b24f2f71ff5c4
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088760B2

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