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

HRID 2071203Notes

Reaction equation

HRID 2071203 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 chloride (0.11 mole) is incrementally added with stirring. After the addition is completed 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 the addition
  5. stirringis completed stirring
  6. filtrationAfter this time the mixture is filtered
  7. washwashed with dilute hydrochloric acid

Sources & evidence

ORD record
ord-410467b56c004d7dbdf40081d2f2db77
Source dataset
uspto-grants-1977_09
Patent number
US04046554

Reaction notes

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