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2-Amino-4-chlorophenol → 5-(5-Chlorobenzoxazol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74208
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 74208
Cl.[CH3:2][C:3]1[N:7]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:6]2[CH:14]=[CH:15][C:16]([C:18]([OH:20])=O)=[CH:17][C:5]=2[N:4]=1.[NH2:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1O.CCN=C=NCCCN(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O.CN(C=O)C>[Cl:28][C:26]1[CH:25]=[CH:24][C:23]2[O:20][C:18]([C:16]3[CH:15]=[CH:14][C:6]4[N:7]([CH:8]5[CH2:9][CH2:10][O:11][CH2:12][CH2:13]5)[C:3]([CH3:2])=[N:4][C:5]=4[CH:17]=3)=[N:21][C:22]=2[CH:27]=1
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Komponenten

8

Edukt 4

HCID 72652-Amino-4-chlorophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 674984452-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt

Produkt 1

HCID 674980045-(5-Chlorobenzoxazol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazoleAusbeute 15,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt (see Working Example 4-3) (0.25 g, 0.96 mmol), 2-amino-4-chlorophenol (0.15 g, 1.05 mmol), anhydrous DMF (10 mL) and WSC (0.22 g, 1.14 mmol) were stirred overnight at room temperature. After the reaction was complete, water (50 mL) was added, the precipitated crystals were filtered off, and the filter residue was extracted with water/chloroform. After the organic layer was dried over anhydrous sodium sulfate, filtration and concentration gave crystals that were dissolved in toluene (5 mL), to which p-toluenesulfonic acid hydrate (0.32 g, 1.68 mmol) was added and this was stirred at reflux for 2 hours. After the solvent was concentrated at reduced pressure, water (5 mL) was added and the solid obtained was filtered off, and after washing with water, drying at reduced pressure at 50° C. yielded the title compound (54 mg, 15.3% yield) as a light brown solid.

Aufarbeitung

  1. filtrationthe precipitated crystals were filtered off
  2. extractionthe filter residue was extracted with water/chloroform
  3. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate, filtration and concentration
  4. customgave crystals that
  5. additionwas added
  6. temperatureat reflux for 2 hours
  7. concentrationAfter the solvent was concentrated at reduced pressure, water (5 mL)
  8. additionwas added
  9. customthe solid obtained
  10. filtrationwas filtered off
  11. washafter washing with water
  12. customdrying at reduced pressure at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-1c725ea87fce4efa883236e0088e42b4
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08829035B2

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