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

HRID 1034291Notes

Reaction equation

HRID 1034291 reaction equation
Cl.[NH2:2][NH2:3].CCN([CH2:9][CH3:10])CC.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1.CC[O:22][CH2:23]C.[C:25]1(C)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:2]([C:25]2[CH:26]=[CH:27][C:28]([O:22][CH2:23][CH:9]=[CH2:10])=[CH:29][CH:30]=2)[NH2:3])=[CH:14][CH:13]=1

Participants

6

Reactant 5

HCID 1140TolueneHCID 3283Diethyl EtherHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 8471TriethylamineHCID 115031Hydrazinium chloride

Product 1

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

Procedure

To a suspension of the hydrazine hydrochloride of Step 1 (70 g) in toluene (1.2 L) 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 (1.2 L) 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-1d1977e11c334f1a9db5a5b9f98751fd
Source dataset
uspto-grants-1994_05
Patent number
US05314900

Reaction notes

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