Aniline → HCID 11019013, compound

HRID 745700Notes

Reaction equation

HRID 745700 reaction equation
[CH:1](=O)[CH:2]([CH3:4])[CH3:3].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN(C)CC1C=CC=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH:1](=[N:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 6115AnilineHCID 6561IsobutyraldehydeHCID 7681N,N-DimethylbenzylamineHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 11019013HCID 11019013, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

144 g (2 mols) of isobutyraldehyde were added dropwise to a solution of 92 g (1 mol) of aniline, 250 ml of methylene chloride, 2 ml of dimethylbenzylamine and 150 g of anhydrous magnesium sulphate at 0° C. in the course of 1 hour, whilst stirring. The mixture was further stirred at from 0° to 10° C. for 5 hours and was filtered, and the residue was rinsed with 200 ml of methylene chloride. The combined organic phases were freed from solvent, in vacuo, at from 30° to 40° C. 155 g of crude N-isobutylideneaniline were obtained and were directly further reacted.

Workup

  1. stirringThe mixture was further stirred at from 0° to 10° C. for 5 hours
  2. filtrationwas filtered
  3. washthe residue was rinsed with 200 ml of methylene chloride
  4. customwere freed from solvent, in vacuo, at from 30° to 40° C

Sources & evidence

ORD record
ord-9bb60a20e2384b798d5d269d4f373f45
Source dataset
uspto-grants-1986_07
Patent number
US04599448

Reaction notes

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