Imidazole → HCID 67859752, compound

HRID 1613267Notes

Reaction equation

HRID 1613267 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18]Cl)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1>COCCOCCOC>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 537387314'-Chloro-4-chloropropoxybenzophenone

Product 1

HCID 67859752HCID 67859752, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of the 4'-chloro-4-chloropropoxybenzophenone (3.0 g, 9.7 mmol) and imidazole (1.3 g, 19 mmol) in 2-methoxyethyl ether (20 mL) 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 1.2 g (36%) of the title compound as a white solid. m.p. 210°-212° C. IR (KBr): 1645, 1601cm-1. MS: 341 (MH) . 1H NMR (CD3OD): δ9.00(s,1H), 7.89-6.87(m,10H), 4.11(t,2H), 3.45(t,2H), 2.11(m,2H).

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-4df6b90d80a84a9aa6e3473e8a1688de
Source dataset
uspto-grants-1993_03
Patent number
US05192786

Reaction notes

Loading…