2,4,5-Triphenylimidazole → 7-(1,2,4-Triphenyl-imidazolyl)-hept-5-ynoic acid

HRID 1376364

Reaktionsgleichung

Reaktionsgleichung von HRID 1376364
[C:1]1([C:7]2[NH:8][C:9](C3C=CC=CC=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[OH-].[K+].Br[CH2:29][C:30]#[C:31][CH2:32][CH2:33][CH2:34][C:35]([O:37]C)=[O:36]>CO>[C:1]1([N:8]2[C:9]([CH2:29][C:30]#[C:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=[C:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 102322,4,5-TriphenylimidazoleHCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 11287432Methyl 7-bromohept-5-ynoate

Produkt 1

HCID 536889797-(1,2,4-Triphenyl-imidazolyl)-hept-5-ynoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 2,4,5-triphenylimidazole (1.07 g) in dimethyl-formimide (20 ml) was treated with sodium hydride 50% in oil (0.17 g) and methyl 7-bromohept-5-ynoate (0.95 g). The solution was stirred for 18 hours when the solvent was removed under reduced pressure and the residue was chromatographed on silica gel eluted with chloroform hexane to give a clear oil which was dissolved in methanol (20 ml) and treated with 10% potassium hydroxide solution (10 ml) for 2 hours. The methanol was removed under reduced pressure and the remaining aqueous was acidified (pH 3) and filtered. The filtrate was extracted with chloroform (3×50 ml). The chloroform extracts were dried over magnesium sulphate, filtered and the solvent removed to give a solid which was recrystallised from acetonitrile to give 7-(1,2,4-triphenyl-imidazolyl)-hept-5-ynoic acid as white prisms, m.p. 144°-145° C.; Found: C, 79.99; H, 5.81; N, 6.40% (C28H24N2O2);Requires: C, 79.97; H, 5.75; N, 6.66%

Aufarbeitung

  1. customwas removed under reduced pressure
  2. customthe residue was chromatographed on silica gel
  3. washeluted with chloroform hexane
  4. customto give a clear oil which
  5. customThe methanol was removed under reduced pressure
  6. filtrationfiltered
  7. extractionThe filtrate was extracted with chloroform (3×50 ml)
  8. dry with materialThe chloroform extracts were dried over magnesium sulphate
  9. filtrationfiltered
  10. customthe solvent removed
  11. customto give a solid which
  12. customwas recrystallised from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-5267751af1ed4384aa2f4197c04d07a6
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663053

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