Dichloromethane → 1-(4-Chlorobenzyl)-1-[4-(pyrid-2-ylmethoxy)phenyl] hydrazine

HRID 1975739Notes

Reaction equation

HRID 1975739 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][NH2:16])=[CH:11][CH:10]=1.C(N(C(C)C)CC)(C)C.ClCCl.[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][N:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:10][CH:11]=2)[NH2:16])=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 6344Dichloromethane2×HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 81531DiisopropylethylamineHCID 190983394-(Pyrid-2-ylmethoxy)phenylhydrazine

Product 1

HCID 190983301-(4-Chlorobenzyl)-1-[4-(pyrid-2-ylmethoxy)phenyl] hydrazine

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

4-(Pyrid-2-ylmethoxy)phenylhydrazine (66.2 g; 308 mmol), prepared as in step 3, was added to a solution of 86 mL diisopropylethylamine and 900 mL dichloromethane. 4-Chlorobenzyl chloride (74.4 g; 462 mmol) and tetrabutylammonium bromide (29.8 g; 92.4 mmol) and an additional 100 mL dichloromethane were added and the reaction was stirred at ambient temperature for 24 hours. The reaction mixture was diluted with water and the layers were separated. The aqueous layer was extracted with dichloromethane. The combined organics were dried over magnesium sulfate and concentrated. The residue was washed with 9:1 diethyl ether, methanol to afford 1-(4-chlorobenzyl)-1-[4-(pyrid-2-ylmethoxy)phenyl] hydrazine as a beige solid.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. concentrationconcentrated
  5. washThe residue was washed with 9:1 diethyl ether, methanol

Sources & evidence

ORD record
ord-42eb282e965041b39511e86f250fb8c1
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

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