Hydrochloric Acid → 1-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine hydrochloride

HRID 77498

Reaction equation

HRID 77498 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C.Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O.C(OCC)C.O1CCOCC1>[ClH:12].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[NH2:11])=[CH:15][CH:14]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 81531DiisopropylethylamineHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 189475691-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine hydrochloride

Reagents, catalysts & solvents 5

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-Methoxyphenylhydrazine hydrochloride (10.0 g, 57.3 mmol), 4-chlorobenzylchloride (9.2 g, 57.2 mmol), tetrabutylammonium bromide (30.7 g, 11.5 mmol), and diisopropylethylamine (20 mL, 115 mmol) in CH2Cl2 (250 mL) was stirred at room temperature for several days. The reaction mixture was diluted with water and the organic layer was dried over MgSO4, filtered, and concentrated. The residue was taken up in toluene (200 mL) and diethyl ether (100 mL), and 1 equivalent of 4N HCl in dioxane was added at 0° C. The mixture was stirred at room temperature for 2 hours, and then evaporated to dryness to give the desired product (C-1; X═Cl) as a purple solid.

Workup

  1. dry with materialthe organic layer was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-aa3a6fcfab7f4ae288aee51a9ed94b8b
Source dataset
uspto-grants-2014_09
Patent number
US08841295B2

Linked notes

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