Benzene → 2-(N-alpha-bromopropionyl-2,3,6-trimethylanilino)acetaldehyde

HRID 1658961Notes

Reaction equation

HRID 1658961 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]([CH3:13])[C:3]=1[NH:4][CH2:5][CH:6]=[O:7].C(=O)([O-])[O-].[Na+].[Na+].C1C=CC=CC=1.[Br:26][CH:27]([CH3:31])[C:28](Cl)=[O:29]>O>[Br:26][CH:27]([CH3:31])[C:28]([N:4]([CH2:5][CH:6]=[O:7])[C:3]1[C:8]([CH3:13])=[CH:9][CH:10]=[C:11]([CH3:12])[C:2]=1[CH3:1])=[O:29]

Participants

6

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 979802-Bromopropanoyl chlorideHCID 214128082-(2,3,6-Trimethylanilino)acetaldehyde

Product 1

HCID 214128092-(N-alpha-bromopropionyl-2,3,6-trimethylanilino)acetaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dimethyl acetal of 2-(2,3,6-trimethylanilino)-acetaldehyde (0.1 mole), sodium carbonate (0.06 mole) dissolved in water (50 ml) and benzene (50 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and cooling means. The mixture is cooled to a temperature of about 0°C and α-bromopropionyl cloride (0.11 mole) is incrementally added with stirring. After addition is is competed stirring is continued and the reaction mixture is permitted to warm to room temperature. After this time the mixture is filtered, washed with dilute hydrochloric acid and stripped of solvent to yield the desired product the dimethyl acetal of 2-(N-α-bromopropionyl-2,3,6-trimethylanilino)acetaldehyde.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and cooling means
  3. additionis incrementally added
  4. additionAfter addition
  5. stirringis is competed stirring
  6. filtrationAfter this time the mixture is filtered
  7. washwashed with dilute hydrochloric acid

Sources & evidence

ORD record
ord-269f5095c05e4ddba79a5b2319ee2b1b
Source dataset
uspto-grants-1976_06
Patent number
US03966811

Reaction notes

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