Benzene → 3-[N-(alpha-chloroacetyl)-2-methyl-4-chloroanilino]propionaldehyde

HRID 1576941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1576941
[CH3:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[NH:4][CH2:5][CH2:6][CH:7]=[O:8].C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:26][CH2:27][C:28](Cl)=[O:29]>O>[Cl:26][CH2:27][C:28]([N:4]([CH2:5][CH2:6][CH:7]=[O:8])[C:3]1[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:2]=1[CH3:1])=[O:29]

Komponenten

6

Edukt 4

HCID 241BenzeneHCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 215102843-(2-Methyl-4-chloroanilino)propionaldehyde

Produkt 1

HCID 215103023-[N-(alpha-chloroacetyl)-2-methyl-4-chloroanilino]propionaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

The diethyl acetal of 3-(2-methyl-4-chloroanilino)propionaldehyde (0.2 mole), benzene (150 ml) and sodium carbonate (0.2 mole) dissolved in water (50 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. The mixture is cooled in an ice bath and chloroacetyl chloride (0.2 mole) is added dropwise with stirring. After addition is completed stirring is continued and the reaction mixture is allowed to warm up to room temperature. After this time the mixture is filtered and the filtrate washed with dilute aqueous hydrochloric acid. The washed filtrate is dried over anhydrous magnesium sulphate and is stripped of solvent under reduced pressure to yield the desired product the diethyl acetal of 3-[N-(α-chloroacetyl)-2-methyl-4-chloroanilino]propionaldehyde.

Aufarbeitung

  1. additionare charged into a glass reaction vessel
  2. customequipped with a mechanical stirrer
  3. additionthermometer and addition funnel
  4. temperatureThe mixture is cooled in an ice bath
  5. additionAfter addition
  6. stirringis completed stirring
  7. filtrationAfter this time the mixture is filtered
  8. washthe filtrate washed with dilute aqueous hydrochloric acid
  9. dry with materialThe washed filtrate is dried over anhydrous magnesium sulphate

Quellen und Nachweise

ORD-Eintrag
ord-cce2c93df68940aaa0229d13e320629c
Quelldatensatz
uspto-grants-1976_09
Patentnummer
US03983174

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