Imidazole → 1-[2-Cyano-2-(4-phenylthiophenyl)hexyl]imidazole

HRID 128226Notes

Reaction equation

HRID 128226 reaction equation
[C:1]([C:3]([C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4]Br)#[N:2].[NH:23]1[CH:27]=[CH:26][N:25]=[CH:24]1>O>[C:1]([C:3]([C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)#[N:2]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 542149592-Cyano-2-(4-phenylthiophenyl)hexyl bromide

Product 1

HCID 540197231-[2-Cyano-2-(4-phenylthiophenyl)hexyl]imidazoleYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g (0.027 mole) of 2-cyano-2-(4-phenylthiophenyl)hexyl bromide and 8 g (0.13 mole) of imidazole is heated with stirring at 160° for four hours. The reaction mixture is poured into water and extracted with ether. The combined ether extracts are washed with water and dried over Na2SO4. The drying agent is filtered and to the filtrate is bubbled dry hydrogen chloride gas until solution is strongly acidic. The hydrochloride salt is washed with ether and back neutralized with dilute ammonium hydroxide solution to give 8 g of pure product.

Workup

  1. temperatureis heated
  2. extractionextracted with ether
  3. washThe combined ether extracts are washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationThe drying agent is filtered and to the filtrate
  6. customis bubbled dry hydrogen chloride gas until solution
  7. washThe hydrochloride salt is washed with ether

Sources & evidence

ORD record
ord-b1883a291f8f49158cdfcc690bf2f2d1
Source dataset
uspto-grants-1981_03
Patent number
US04259339

Reaction notes

Loading…