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Bromotrimethylsilane → [6-Chloro-5-(4-chloro-3-methyl-phenyl)-1H-benzoimidazol-2ylsulfanylmethyl]-phosphonic acid

HRID 2193855
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2193855
C([O:3][P:4]([CH2:9][S:10][C:11]1[NH:15][C:14]2[CH:16]=[C:17]([Cl:28])[C:18]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([CH3:27])[CH:21]=3)=[CH:19][C:13]=2[N:12]=1)(=[O:8])[O:5]CC)C.Br[Si](C)(C)C>C(Cl)Cl.C[Si](C)(C)N[Si](C)(C)C>[Cl:28][C:17]1[C:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([CH3:27])[CH:21]=2)=[CH:19][C:13]2[N:12]=[C:11]([S:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5])[NH:15][C:14]=2[CH:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 76113BromotrimethylsilaneHCID 86657369[6-Chloro-5-(4-chloro-3-methyl-phenyl)-1H-benzoimidazol-2-ylsulfanylmethyl]-phosphonic acid diethyl ester

Produkt 1

HCID 58422973[6-Chloro-5-(4-chloro-3-methyl-phenyl)-1H-benzoimidazol-2ylsulfanylmethyl]-phosphonic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel
HCID 13838
Hexamethyldisilazane
Lösungsmittel

Versuchsvorschrift

To a solution of [6-Chloro-5-(4-chloro-3-methyl-phenyl)-1H-benzoimidazol-2-ylsulfanylmethyl]-phosphonic acid diethyl ester 12-1 (140 mg, 0.29 mmol) in CH2Cl2 (0.8 mL) and hexamethyldisilazane (0.8 mL) was added bromotrimethylsilane (0.40 mL, 3.0 mmol). After stirring overnight at room temperature, the volatiles were removed from the mixture via a rotary evaporator. The resulting residue was dissolved in EtOAc (2 mL) and filtered through a 0.45 μm syringe filter. The filtrate was evaporated to dryness, and anhydrous MeOH was added. The mixture was triturated by sonication from MeOH to give a suspension of a fine white solid. The solid was isolated by centrifugation followed by decanting the MeOH. The resulting solid was furthered purified by a second trituration in MeOH, and then dried under vacuum at 40° C. overnight to afford the title compound 12-2. LRMS (API-ES) m/e for C15H13Cl2N2O3PS (M+H)+, calcd 403.23. found 403.1. Anal. Calcd for C15H13Cl2N2O3PS: C, 44.68; H, 3.25; N, 6.95. Found: C, 44.44; 1-1, 3.43; N, 6.68.

Aufarbeitung

  1. customthe volatiles were removed from the mixture via a rotary evaporator
  2. dissolutionThe resulting residue was dissolved in EtOAc (2 mL)
  3. filtrationfiltered through a 0.45 μm syringe
  4. filtrationfilter
  5. customThe filtrate was evaporated to dryness, and anhydrous MeOH
  6. additionwas added
  7. customThe mixture was triturated by sonication from MeOH
  8. customto give
  9. additiona suspension of a fine white solid
  10. customThe solid was isolated by centrifugation
  11. customby decanting the MeOH
  12. customThe resulting solid was furthered purified by a second trituration in MeOH
  13. customdried under vacuum at 40° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-8a33a54f42674f2d8570eb2121158dce
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08329914B2

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