Potassium Carbonate → N-(p-Bromobenzyl)-N-(4-methoxyphenyl)hydrazine hydrochloride

HRID 1451532Notes

Reaction equation

HRID 1451532 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:1].[Br: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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 19041688N-(p-Bromobenzyl)-N-(4-methoxyphenyl)hydrazine hydrochlorideYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-methoxyphenylhydrazine hydrochloride (459 g, 2.63 mol), p-bromobenzyl bromide (715 g, 2.86 mol) and milled potassium carbonate (771 g, 5.58 mol) was suspended in 2 L DMF at 0° C. with overhead stirring. The ice bath was removed and the mixture was stirred for 4 h, then diluted with 15 L of ice water. The mixture was stirred vigourously for 1 h, then the aqueous layer was decanted from the gummy solid. The solid was washed with 2×4 L of water, then was dissolved in 2.5 L toluene and dried over Na2SO4. The mixture was filtered, and the filtrate was cooled in an ice bath and treated with a stream of HCl gas for 1 h with vigourous stirring. The precipitate was filtered and-washed with 3×0.5 L of cold toluene and dried under a stream of nitrogen to give 682 g of the title compound.

Workup

  1. customThe ice bath was removed
  2. additiondiluted with 15 L of ice water
  3. stirringThe mixture was stirred vigourously for 1 h
  4. customthe aqueous layer was decanted from the gummy solid
  5. washThe solid was washed with 2×4 L of water
  6. dissolutionwas dissolved in 2.5 L toluene
  7. dry with materialdried over Na2SO4
  8. filtrationThe mixture was filtered
  9. temperaturethe filtrate was cooled in an ice bath
  10. additiontreated with a stream of HCl gas for 1 h with vigourous stirring
  11. filtrationThe precipitate was filtered
  12. wash-washed with 3×0.5 L of cold toluene
  13. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-cac762c0071d4362ab112171be85722e
Source dataset
uspto-grants-1997_02
Patent number
US05604253

Reaction notes

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