(4-Methoxyphenyl)hydrazine → HCID 21449355, compound

HRID 597069Notes

Reaction equation

HRID 597069 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[Cl:11][C:12]1[N:17]=[C:16](Cl)[CH:15]=[C:14]([Cl:19])[N:13]=1.C([O-])(=O)C.[Na+]>O.C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:16]2[CH:15]=[C:14]([Cl:19])[N:13]=[C:12]([Cl:11])[N:17]=2)[NH2:10])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 77023(4-Methoxyphenyl)hydrazineHCID 773782,4,6-TrichloropyrimidineHCID 517045Sodium Acetate

Product 1

HCID 21449355HCID 21449355, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of p-methoxyphenylhydrazine (59 g.), 2,4,6-trichloropyrimidine (78.5 g.), and a solution of anhydrous sodium acetate (63 g.) in a mixture of water (260 ml.) and ethanol (1200 ml.) was shaken at room temperature for 2 hours. The crystalline precipitate which had formed was collected by filtration, washed with ethanol (50 ml.) and recrystallised from a mixture of chloroform (200 ml.) and ethanol (800 ml.) to give N-(p-methoxyphenyl)-N-(2,6-dichloropyrimidin-4-yl)hydrazine as a pale yellow solid, m.p. 156°-158° C. From the crystallisation mother liquors there was obtained, after chromatography on silica gel (300 g.) using a mixture containing equal parts by volume of ether and petroleum ether (b.p. 40° C.), N-(p-methoxyphenyl)-N-(4,6-dichloropyrimidin-2-ylhydrazine as a pale yellow solid, m.p. 113°-115° C.

Workup

  1. customThe crystalline precipitate which had formed
  2. filtrationwas collected by filtration
  3. washwashed with ethanol (50 ml.)
  4. customrecrystallised from a mixture of chloroform (200 ml.) and ethanol (800 ml.)

Sources & evidence

ORD record
ord-17d171178bb44f72b3c34d1c8df658ff
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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