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

HRID 76898Notes

Reaction equation

HRID 76898 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bc6ac48b2f6147e59933a2373b2fcd50
Source dataset
uspto-grants-2014_09
Patent number
US08835646B2

Reaction notes

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