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Probenecid → 4-Dipropylsulfamoyl-N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-benzamide

HRID 1060279
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1060279
[CH2:1]([N:4]([CH2:17][CH2:18][CH3:19])[S:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH2:2][CH3:3].S(Cl)(Cl)=O.[NH2:24][C:25]1[S:26][C:27]2[C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:32][CH:31]=[C:30]([O:40][CH3:41])[C:28]=2[N:29]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH2:17]([N:4]([CH2:1][CH2:2][CH3:3])[S:5]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:24][C:25]2[S:26][C:27]3[C:33]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:32][CH:31]=[C:30]([O:40][CH3:41])[C:28]=3[N:29]=2)=[O:14])=[CH:15][CH:16]=1)(=[O:6])=[O:7])[CH2:18][CH3:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 4911ProbenecidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 222830262-Amino-4-methoxy-7-phenyl-benzothiazole

Produkt 1

HCID 222830654-Dipropylsulfamoyl-N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-benzamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of 4-dipropylsulfamoyl-benzoic acid (185 mg, 0.65 mmol) in toluene (10 ml) was added thionylchloride (600 mg, 5 mmol) and the mixture heated to 80° C. for 17 h. After cooling the solvent was evaporated and the resudue was taken up in THF (20 ml), 2-amino-4-methoxy-7-phenyl-benzothiazole (128 mg, 0.5 mmol), triethylamine (105 μl, 0.75 mmol), and DMAP (6 mg, 0.05 mmol) were then added and the mixture was stirred for 1 hour at r.t. followed by 1 hour at 60° C. After cooling to r.t. the reaction mixture was quenched by addition of 10% aq. Na2CO3 solution (30 ml) and EtOAc (30 ml) and vigorous stirring. After separation of the phases the aqueous phase was extracted with EtOAc (30 ml) and the combined orgainc phases were washed with 10% aq. Na2CO3, dried with Na2SO4, filtered and evaporated. The residue was then chromatographed over SiO2 (Merck 230-400 mesh) eluting with a gradient of cyclohexane/EtOAc from (1:4) to 100% EtOAc. After pooling and evaporation of the product fractions the title compound was obtained as a white solid (240 mg, 92% yield), MS: m/e=524.2 (M+H+).

Aufarbeitung

  1. temperatureAfter cooling the solvent
  2. customwas evaporated
  3. waitfollowed by 1 hour at 60° C
  4. temperatureAfter cooling to r.t. the reaction mixture
  5. customwas quenched by addition of 10% aq. Na2CO3 solution (30 ml) and EtOAc (30 ml) and vigorous stirring
  6. customAfter separation of the phases the aqueous phase
  7. extractionwas extracted with EtOAc (30 ml)
  8. washthe combined orgainc phases were washed with 10% aq. Na2CO3
  9. dry with materialdried with Na2SO4
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was then chromatographed over SiO2 (Merck 230-400 mesh)
  13. washeluting with a gradient of cyclohexane/EtOAc from (1:4) to 100% EtOAc
  14. customevaporation of the product fractions the title compound

Quellen und Nachweise

ORD-Eintrag
ord-366761ca515c4e5086827acf8cf75c1f
Quelldatensatz
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06521754B2

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