Water → HCID 22916337, compound

HRID 265360Notes

Reaction equation

HRID 265360 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:10]=[C:9]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C-:31]#[N:32].[Na+].O>CS(C)=O>[C:31]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:10]=[C:9]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)#[N:32]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 22916349HCID 22916349, compound

Product 1

HCID 22916337HCID 22916337, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

1-(6-Bromohexyl)-2,4,5-triphenylimidazole (27.6 g) in dry dimethylsulphoxide (70 ml) was added over 10 minutes to a mixture of sodium cyanide (3.68 g) in dimethyl-sulphoxide (50 ml) and the reaction was stirred at room temperature for 20 h. The reaction mixture was poured into water (300 ml) and extracted with dichloromethane (3×150 ml). The extracts were combined, washed with water, dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo. Recrystallisation from diethyl ether and hexane gave 1-(6-cyanohexyl)-2,4,5-triphenylimidazole (24.19 g, 99%) as a white solid, m.p. 104°-6°.

Workup

  1. extractionextracted with dichloromethane (3×150 ml)
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customevaporated to dryness in vacuo
  5. customRecrystallisation from diethyl ether and hexane

Sources & evidence

ORD record
ord-7163798052104b92af02fac52740c95d
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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