2,6-Dimethylaniline → HCID 21412829, compound

HRID 1576932Notes

Reaction equation

HRID 1576932 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 (100 grams), the diethyl acetal of 2-bromoacetaldehyde (59.1 grams) and sodium carbonate (31.8 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The mixture was heated at a temperature of about 150°C for a period of about 30 hours. After this time the reaction mixture was cooled to room temperature and was filtered. The filtrate was then distilled under vacuum to yield the desired product the diethyl acetal of 2-(2,6-dimethylanilino)acetaldehyde as the residue.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureAfter this time the reaction mixture was cooled to room temperature
  4. filtrationwas filtered
  5. distillationThe filtrate was then distilled under vacuum

Sources & evidence

ORD record
ord-924425a42ab94d1cb586d35638f22c09
Source dataset
uspto-grants-1976_09
Patent number
US03983174

Reaction notes

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