2,6-Dimethylaniline → HCID 21412829, compound

HRID 1658957Notes

Reaction equation

HRID 1658957 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].Br[CH2:11][CH:12]=[O:13].C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][CH2:11][CH:12]=[O:13]

Participants

4

Reactant 3

HCID 68962,6-DimethylanilineHCID 10340Sodium CarbonateHCID 105131Acetaldehyde, bromo-

Product 1

HCID 21412829HCID 21412829, compound

Conditions

Temperature
150 °C

Procedure

2,6-Dimethylaniline (80 grams), the diethyl acetal of 2-bromoacetaldehyde (59.1 grams) and sodium carbonate (25.2 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at 150°C for a period of about 30 hours. After this time the mixture was filtered and the filtrate was distilled to yield the desired product the diethyl acetal of 2-(2,6-dimethylanilino)acetaldehyde as a brown tarry solid.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. filtrationAfter this time the mixture was filtered
  4. distillationthe filtrate was distilled

Sources & evidence

ORD record
ord-6d978f11d40c49c9bf72c311741a691d
Source dataset
uspto-grants-1976_06
Patent number
US03966811

Reaction notes

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