Hydrazine → N-Benzyl-N-phenylhydrazine

HRID 543520Notes

Reaction equation

HRID 543520 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.C(C1OC(C2C=CC=CC=2)C(C2C=CC=CC=2)[N:23]=1)=O>C(O)C.C(O)(=O)C.[Zn]>[CH2:1]([N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH2:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 9321HydrazineHCID 66028BenzylanilineHCID 20461729HCID 20461729, compound

Product 1

HCID 69192N-Benzyl-N-phenylhydrazineYield 17.8%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

1-benzyl-1-phenylhydrazine was prepared in the same manner as Synthesis Example 1 except for using 208.6 g (1.14 mol) of N-benzylaniline in place of diphenylamine. Said hydrazine was dissolved in a mixture of 1 l of ethanol and 50 ml of acetic acid, and 286 g (1.14 mol) of 2-formyl-4,5-diphenyloxazoline, represented by the formula ##STR9## was added. The resulting mixture was cooled to 10° C., and 250 g (3.82 mol) of zinc metal was added with caution not to raise the temperature over 20° C. After completion of the reaction, the reaction mixture was filtered and the filtrate was poured into water, thus giving a yellow precipitate. Recrystallization of the precipitate from a methyl ethyl ketone-ethanol (1:1) mixture gave 87.5 g of yellow crystals (yield 17.8% based on the amine).

Workup

  1. additionwas added
  2. temperatureto raise the temperature over 20° C
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtered
  5. additionthe filtrate was poured into water
  6. customthus giving a yellow precipitate
  7. customRecrystallization of the precipitate from a methyl ethyl ketone-ethanol (1:1) mixture

Sources & evidence

ORD record
ord-cb8668eb893e440c94ac20cbd5c9f9ca
Source dataset
uspto-grants-1984_05
Patent number
US04446217

Reaction notes

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