Toluene → 1-[(4-Chlorophenyl)methyl]-1-{4-[(prop-2-en-1-yl)oxy]phenyl}hydrazine

HRID 1590087Notes

Reaction equation

HRID 1590087 reaction equation
[NH2:1][NH2:2].CCN([CH2:8][CH3:9])CC.[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1.CC[O:21][CH2:22]C.[C:24]1(C)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:1]([C:24]2[CH:25]=[CH:26][C:27]([O:21][CH2:22][CH:8]=[CH2:9])=[CH:28][CH:29]=2)[NH2:2])=[CH:13][CH:12]=1

Participants

6

Reactant 5

HCID 1140TolueneHCID 3283Diethyl EtherHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 8471TriethylamineHCID 9321Hydrazine

Product 1

HCID 149805221-[(4-Chlorophenyl)methyl]-1-{4-[(prop-2-en-1-yl)oxy]phenyl}hydrazine

Procedure

To a suspension of the hydrazine of Step 1 (70 g) in toluene (1.2L) was added Et3N (107 mL) followed by 4-chlorobenzyl chloride (61 g). The resulting mixture was heated at reflux for 2 hours. The reaction mixture was cooled and Et2O (1.2L) was added. The triethylammonium hydrochloride salt was filtered off, and the filtrate concentrated under vacuum. The crude residue was purified by chromatography on a bed of silica gel eluting with hexane-EtOAc (6:4) to afford the pure title product as an oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe triethylammonium hydrochloride salt was filtered off
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe crude residue was purified by chromatography on a bed of silica gel eluting with hexane-EtOAc (6:4)

Sources & evidence

ORD record
ord-d7809d4972104e6b989fb449d12d26ae
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

Loading…