Allylbenzene → HCID 14426201, compound

HRID 1762280Notes

Reaction equation

HRID 1762280 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N+:15]([O-:17])[CH3:16])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1.[CH2:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:19]=[CH2:20]>C1(C)C=CC=CC=1>[C:21]1([CH2:18][CH:19]2[O:17][N:15]([CH3:16])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)([CH2:9][N:10]3[CH:14]=[CH:13][N:12]=[CH:11]3)[CH2:20]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 9309AllylbenzeneHCID 727271741-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-N-methylethanimine N-oxide

Product 1

HCID 14426201HCID 14426201, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 7.04 g (0.0282 mol) of 1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-N-methylethanimine N-oxide (1: R1 =4-Cl) [prepared by reacting 2-(1H-imidazol-1-yl)-4'-chloroacetophenone (45.05 g, 0.204 mol), N-methylhydroxylamine hydrochloride (20.93 g, 0.251 mol), and sodium acetate (41.13 g, 0.502 mol) in 550 ml of ethanol] and 3.95 g (0.0334 mol) of allylbenzene (2: R2 =CH2C6H5) in 100 ml toluene is refluxed for 30 hours under a nitrogen atmosphere. Upon cooling to room temperature, the solvent is removed in vacuo. The resulting cis-/trans-diastereomeric mixture of compound 3 (R1 =4-Cl, R2 =CH2C6H5 is flash-chromatographed on neutral silica gel using a 98:2 by volume mixture of chloroform and methanol as eluent to give 3.80 g (36%) of isomer A. Following crystallization from ether a melting point of 118°-120° C. is determined.

Workup

  1. customthe solvent is removed in vacuo
  2. additionThe resulting cis-/trans-diastereomeric mixture of compound 3 (R1 =4-Cl, R2 =CH2C6H5
  3. customis flash-chromatographed on neutral silica gel using a 98:2
  4. additionby volume mixture of chloroform and methanol as eluent
  5. customto give 3.80 g (36%) of isomer A
  6. customcrystallization from ether a melting point of 118°-120° C.

Sources & evidence

ORD record
ord-6cc232323e1a49b7aa6eb67e6262ad99
Source dataset
uspto-grants-1989_05
Patent number
US04831154

Reaction notes

Loading…