Thionyl Chloride → 1-(2-Bromobenzyl)-5-(3-chloropropyl)-1H-imidazole

HRID 1877956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1877956
O=S(Cl)[Cl:3].[Br:5][C:6]1[CH:21]=[CH:20][CH:19]=[CH:18][C:7]=1[CH2:8][N:9]1[C:13]([CH2:14][CH2:15][CH2:16]O)=[CH:12][N:11]=[CH:10]1>C(Cl)Cl>[Br:5][C:6]1[CH:21]=[CH:20][CH:19]=[CH:18][C:7]=1[CH2:8][N:9]1[C:13]([CH2:14][CH2:15][CH2:16][Cl:3])=[CH:12][N:11]=[CH:10]1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 588271793-[3-(2-Bromobenzyl)-3H-imidazole-4-yl]propan-1-ol

Produkt 1

HCID 588270851-(2-Bromobenzyl)-5-(3-chloropropyl)-1H-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of SOCl2 (0.55 mL, 7.54 mmol) in CH2Cl2 (15 mL) at 0° C. is added 3-[3-(2-bromobenzyl)-3H-imidazol-4-yl]propan-1-ol in portion and the resulting white suspension is refluxed for 1.5 h. The mixture is cooled with ice and collected to give a buff-colored solid, which is partitioned between CH2Cl2 and saturated aqueous NaHCO3. The organic layer is washed with brine, dried over anhydrous Na2SO4, and concentrated to give an oil. MS (ESI) m/z 313 (M+H).

Aufarbeitung

  1. temperaturethe resulting white suspension is refluxed for 1.5 h
  2. temperatureThe mixture is cooled with ice
  3. customcollected
  4. customto give a buff-colored solid, which
  5. customis partitioned between CH2Cl2 and saturated aqueous NaHCO3
  6. washThe organic layer is washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-08e16eeb61144593bf58b95b3ab526fc
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314097B2

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