Thionyl Chloride → 5-(3-chloropropyl) 1-(p-cyanophenylmethyl)-1H-imidazole

HRID 477967Notes

Reaction equation

HRID 477967 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:18]([CH2:19][CH2:20][CH2:21]O)=[CH:17][N:16]=[CH:15]2)=[CH:9][CH:8]=1)#[N:6]>C(Cl)Cl>[Cl:3][CH2:21][CH2:20][CH2:19][C:18]1[N:14]([CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:5]#[N:6])=[CH:8][CH:9]=2)[CH:15]=[N:16][CH:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 136882083-[1-(4-Cyanobenzyl)-1H-imidazol-5-yl]-1-propanol

Product 1

HCID 136882095-(3-chloropropyl) 1-(p-cyanophenylmethyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.2 g of thionyl chloride in 80 ml of methylene chloride is added 8.4 g of 1-(p-cyanophenylmethyl)-5-(3-hydroxypropyl)-1H-imidazole as a solid in portions. The rate of addition is regulated to control the foaming that occurs. When addition is complete, the solution is refluxed for 1.5 h, cooled in ice and filtered to obtain the hydrochloride salt of the title compound (c) as a buff-colored solid, m.p. 190°-191°. The salt is partitioned between methylene chloride and saturated sodium bicarbonate solution. The organic extracts are washed with water, dried over sodium sulfate and evaporated to yield the free base as an oil.

Workup

  1. additionThe rate of addition
  2. additionWhen addition
  3. temperaturethe solution is refluxed for 1.5 h
  4. temperaturecooled in ice
  5. filtrationfiltered

Sources & evidence

ORD record
ord-877861f32074420c811c7880d33a09ba
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Reaction notes

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