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

HRID 923275Notes

Reaction equation

HRID 923275 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-285de5041cb44758b2992b72115c0219
Source dataset
uspto-grants-2016_03
Patent number
US09278969B2

Reaction notes

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