Phenylhydrazine → HCID 13064194, compound

HRID 2198983Notes

Reaction equation

HRID 2198983 reaction equation
[Na].[C:2]1([NH:8][NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH:14]=[CH:15][C:16]#[N:17]>C(O)C>[NH2:17][C:16]1[CH2:15][CH:14]([C:13]2[CH:18]=[CH:19][C:20]([Cl:21])=[C:11]([Cl:10])[CH:12]=2)[N:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 5360545SodiumHCID 53857603HCID 53857603, compound

Product 1

HCID 13064194HCID 13064194, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 0.10 g. amount of sodium metal is dissolved in 25.0 ml. of absolute ethanol, then 2.16 g. of phenylhydrazine is added, followed in 5 minutes by 3.96 g. of 3,4-dichlorocinnamonitrile. The reaction mixture is refluxed for 5 hours, then is evaporated to dryness in vacuo. The procedure, as described in Example 15, is continued with a second recrystallization from the same solvent pair and treatment with a hydrous magnesium silicate to give 1.35 g. of the desired product as colorless needles, m.p. 150°-151.5° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. customis evaporated to dryness in vacuo
  3. customis continued with a second recrystallization from the same solvent pair and treatment with a hydrous magnesium silicate
  4. customto give 1.35 g

Sources & evidence

ORD record
ord-822587ec73a1493a80e835c358407e1f
Source dataset
uspto-grants-1982_11
Patent number
US04360680

Reaction notes

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