p-Toluidine → HCID 178435944, compound

HRID 1701308Notes

Reaction equation

HRID 1701308 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH2:9]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14])[CH3:10].[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:13](=[NH:14])[C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[CH2:9][CH3:10])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 7813p-ToluidineHCID 14798Sodium HydroxideHCID 1234432-EthylbenzonitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178435944HCID 178435944, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g. of p-toluidine, 6.2 g. of o-ethylbenzonitrile and 6.3 g. of anhydrous aluminum chloride were heated at 120° C. with stirring for 1 hour. To the reaction mixture was added water and sodium hydroxide to make the mixture alkaline. The mixture was extracted with benzene and the extract was washed with water, dried and evaporated in vacuo to remove benzene. 10.2 g. (92% of theory) of N-(p-methylphenyl)-2-ethylbenzamidine was obtained.

Workup

  1. extractionThe mixture was extracted with benzene
  2. washthe extract was washed with water
  3. customdried
  4. customevaporated in vacuo
  5. customto remove benzene

Sources & evidence

ORD record
ord-3579a04783644b109cfbb981a13d44b1
Source dataset
uspto-grants-1980_03
Patent number
US04192880

Reaction notes

Loading…