2,6-Dimethylaniline → HCID 54352736, compound

HRID 1156832Notes

Reaction equation

HRID 1156832 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].Br[CH:17]([CH3:22])[CH:18]=[N:19][O:20][CH3:21]>CN(C)C=O>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[CH3:21][O:20][N:19]=[CH:18][CH:17]([NH:4][C:3]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1])[CH3:22]

Participants

6

Reactant 3

HCID 68962,6-DimethylanilineHCID 11430Potassium CarbonateHCID 54099141HCID 54099141, compound

Product 2

HCID 68962,6-DimethylanilineHCID 54352736HCID 54352736, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

42.4 g (0.35 mol) of 2,6-dimethylaniline and 25 g (0.17 mol) of powdered potassium carbonate in 100 ml of dimethylformamide were heated to 80° C., whilst stirring, and 29 g (0.17 mol) of 2-bromo-1-methoxyimino-propane were added dropwise. During this addition, the temperature rose to 95° C. The mixture was stirred for a further 2 hours at 80° C., the inorganic salt was filtered off and the filtrate was distilled. After distilling off the solvent and the excess 2,6-dimethylaniline, 25.4 g (72.5% of theory) of N-(1-methoxyimino-prop-2-yl)-2,6-dimethylaniline of boiling point 107°-109° C./0.1 mm Hg were obtained. ##STR175## Process variant (a)

Workup

  1. additionDuring this addition
  2. customrose to 95° C
  3. stirringThe mixture was stirred for a further 2 hours at 80° C.
  4. filtrationthe inorganic salt was filtered off
  5. distillationthe filtrate was distilled
  6. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-d50f34879d55491eb9de4a0aca011d02
Source dataset
uspto-grants-1982_06
Patent number
US04337268

Reaction notes

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