Triethylamine → 2-Methoxy-N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-benzamide

HRID 1060270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060270
[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][CH:8]=[C:7]([O:17][CH3:18])[C:5]=2[N:6]=1.C(N(CC)CC)C.[CH3:26][O:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31]>C1COCC1.CN(C1C=CN=CC=1)C>[CH3:26][O:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([NH:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][CH:8]=[C:7]([O:17][CH3:18])[C:5]=2[N:6]=1)=[O:31]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 222830262-Amino-4-methoxy-7-phenyl-benzothiazole

Produkt 1

HCID 222834002-Methoxy-N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2-amino-4-methoxy-7-phenyl-benzothiazole (200 mg, 0.67 mmol) in THF (10 m) was added DMAP (10 mg, 0.08 mmol), triethylamine (163 □l, 1.17 mmol) and 2-methoxybenzoyl chloride (136 □1, 1 mmol) in THF (2 ml). The mixture was then heated to reflux for 2 h, after cooling, it was partitioned between 1:1 AcOEt/THF (70 ml) and 5% NaHCO3 solution( 40 ml). The organic phase was washed with saturated NaCl solution (50 ml), dried with Na2SO4, filtered and the solvent removed under reduced presure. The residue was suspended in ether (10 ml), filtered, washed with ether then dried under vacuum (0.05 mmHg, 60 ° C.), to afford the title compound was a white solid (260 mg, 85% yield), MS: m/e=390.0 (M+).

Aufarbeitung

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 2 h
  3. temperatureafter cooling
  4. customit was partitioned between 1:1 AcOEt/THF (70 ml) and 5% NaHCO3 solution( 40 ml)
  5. washThe organic phase was washed with saturated NaCl solution (50 ml)
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customthe solvent removed
  9. filtrationfiltered
  10. washwashed with ether
  11. customthen dried under vacuum (0.05 mmHg, 60 ° C.)

Quellen und Nachweise

ORD-Eintrag
ord-2c2704a95ed34c91a9a2d462706022cb
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521754B2

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