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

HRID 2290562Notes

Reaction equation

HRID 2290562 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 hours, cooled in ice and filtered to obtain the hydrochloride salt of the title compound (c) as a buff-colored solid, m.p. 190°-191°.

Workup

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

Sources & evidence

ORD record
ord-b97a53247990457580bea94ebe3452c2
Source dataset
uspto-grants-1986_10
Patent number
US04617307

Reaction notes

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