1-Heptyl-1H-imidazole → (Z)-1-[4-(4-Chlorophenyl)-2-butenyl]-3-heptylimidazolium 4-methylbenzenesulfonate

HRID 1380362Notes

Reaction equation

HRID 1380362 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]/[CH:9]=[CH:10]\[CH2:11]O)=[CH:4][CH:3]=1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O-:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.[CH2:24]([N:31]1[CH:35]=[CH:34][N:33]=[CH:32]1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C(#N)C>[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([O-:23])(=[O:22])=[O:21])=[CH:18][CH:19]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][N+:33]2[CH:34]=[CH:35][N:31]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:32]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1866691-Heptyl-1H-imidazoleHCID 131714350(Z)-4-(4-Chlorophenyl)-2-buten-1-ol 4-methylbenzenesulfonate

Product 1

HCID 86740719(Z)-1-[4-(4-Chlorophenyl)-2-butenyl]-3-heptylimidazolium 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add 3.37 g (0.01 mole) of (Z)-4-(4-chlorophenyl)-2-buten-1-ol 4-methylbenzenesulfonate (ester) and 1.50 g (0.009 mole) of 1-heptyl-1H-imidazole in 40 ml of acetonitrile and stir at room temperature for two days. Evaporate the acetonitrile and triturate the residue with hexanes and ethyl acetate to yield a solid. Recrystallize from ethyl acetate to provide the title compound.

Workup

  1. customEvaporate the acetonitrile
  2. customtriturate the residue with hexanes and ethyl acetate
  3. customto yield a solid
  4. customRecrystallize from ethyl acetate

Sources & evidence

ORD record
ord-4ead6bc283be418b906514b43b6d5d22
Source dataset
uspto-grants-1986_04
Patent number
US04581370

Reaction notes

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