Imidazole → (E)-4-(1H-Imidazol-1-yl)butoxystilbene hydrochloride

HRID 1613262Notes

Reaction equation

HRID 1613262 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1>COCCOCCOC>[ClH:1].[N:21]1([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 19775673HCID 19775673, compound

Product 1

HCID 19775671(E)-4-(1H-Imidazol-1-yl)butoxystilbene hydrochlorideYield 108.7%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of the (E)-4-chlorobutoxystilbene (2.0 g, 7.0 mmol) and imidazole (1.0 g, 14 mmol) in 20 mL of 2-methoxyethyl ether was heated to 120° C. for 24 hours. The solvent was removed by distillation and the resulting residue was chromatographed (flash, SiGel, 9:1 CH2Cl2 -MeOH). The hydrochloride salt was made in HCl/MeOH and recrystallized from acetone to give 2.7 g (95%) of the title compound as an off-white solid. m.p. 208°-210° C. IR(KBr): 3400,1590cm-1. MS: 319(MH)+. 1H NMR(CD3OD): δ9.21(s,1H), 7.65-6.82(m,13H), 4.35(t,2H), 4.02 (t,2H), 2.01(m,4H).

Workup

  1. customThe solvent was removed by distillation
  2. customthe resulting residue was chromatographed (flash, SiGel, 9:1 CH2Cl2 -MeOH)
  3. customrecrystallized from acetone

Sources & evidence

ORD record
ord-7c4e307cb55d4c8ab613f41445586c5a
Source dataset
uspto-grants-1993_03
Patent number
US05192786

Reaction notes

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