Sodium Carbonate → 2-(2,6-Diethylanilino)acetaldehyde

HRID 1576934Notes

Reaction equation

HRID 1576934 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH2:5])[CH3:2].Br[CH2:13][CH:14]=[O:15].C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH:5][CH2:13][CH:14]=[O:15])[CH3:2]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 113692,6-DiethylanilineHCID 105131Acetaldehyde, bromo-

Product 1

HCID 214128262-(2,6-Diethylanilino)acetaldehyde

Conditions

Temperature
150 °C

Procedure

2,6-Diethylaniline (120 grams), the diethyl acetal of 2-bromoacetaldehyde (78.8 grams) and sodium carbonate (42.4 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-diethylanilino)acetaldehyde as the residue having a boiling point of 130°C at 1 mm of Hg pressure.

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-764ef7af423f4ebc88735eea890ab4d0
Source dataset
uspto-grants-1976_09
Patent number
US03983174

Reaction notes

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