Thionyl Chloride → 6-[5-(3-Chloropropyl)imidazol-1-ylmethyl]biphenyl-3-carbonitrile

HRID 923281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 923281
O=S(Cl)[Cl:3].O[CH2:6][CH2:7][CH2:8][C:9]1[N:13]([CH2:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:19][C:18]([C:27]#[N:28])=[CH:17][CH:16]=2)[CH:12]=[N:11][CH:10]=1>C(Cl)Cl>[Cl:3][CH2:6][CH2:7][CH2:8][C:9]1[N:13]([CH2:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:19][C:18]([C:27]#[N:28])=[CH:17][CH:16]=2)[CH:12]=[N:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 588272366-[5-(3-Hydroxypropyl)imidazol-1-ylmethyl]biphenyl-3-carbonitrile

Produkt 1

HCID 588270706-[5-(3-Chloropropyl)imidazol-1-ylmethyl]biphenyl-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of SOCl2 (0.382 mL, 5.24 mmol) in CH2Cl2 (20 mL) at 0° C. is added 6-[5-(3-hydroxypropyl)imidazol-1-ylmethyl]biphenyl-3-carbonitrile in portion and the resulting white suspension is refluxed for 1.5 h. The mixture is cooled in ice and partitioned between CH2Cl2 and saturated aqueous NaHCO3. The organic layer is washed with brine, dried over anhydrous Na2SO4 and concentrated to give an oily foam.

Aufarbeitung

  1. temperaturethe resulting white suspension is refluxed for 1.5 h
  2. temperatureThe mixture is cooled in ice
  3. custompartitioned between CH2Cl2 and saturated aqueous NaHCO3
  4. washThe organic layer is washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customto give an oily foam

Quellen und Nachweise

ORD-Eintrag
ord-61c1fe259fe346d29b553bef2f25c04e
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278969B2

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