Chloroacetyl chloride → 2-Chloro-N-(2,6-diethylphenyl)-N-[(1,3-dioxolan-2-yl)methyl]acetamide

HRID 1578910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1578910
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH:7][C:8]1[C:13]([CH2:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:16][CH3:17].C(=O)(O)[O-].[Na+].O1CCOCC1.[Cl:29][CH2:30][C:31](Cl)=[O:32]>CCOCC.O>[Cl:29][CH2:30][C:31]([N:7]([CH2:6][CH:2]1[O:3][CH2:4][CH2:5][O:1]1)[C:8]1[C:9]([CH2:16][CH3:17])=[CH:10][CH:11]=[CH:12][C:13]=1[CH2:14][CH3:15])=[O:32]

Komponenten

7

Edukt 4

HCID 6577Chloroacetyl chlorideHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 21548997N-(1,3-dioxolan-2-ylmethyl)-2,6-diethylaniline

Produkt 1

HCID 202845692-Chloro-N-(2,6-diethylphenyl)-N-[(1,3-dioxolan-2-yl)methyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

N-(1,3-dioxolan-2-ylmethyl)-2,6-diethylaniline (7.7 grams), sodium bicarbonate (6.0 grams), dioxane (20 ml) and water (4 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. This mixture was cooled to a temperature of about 0°C and chloroacetyl chloride (4.0 grams) was added, with stirring, over a period of about 15 minutes. After the addition was completed stirring was continued for a period of about 1 hour. After this time ether (100 ml) was added to the mixture and the resulting solution was washed with water. The washed solution was then dried over anhydrous magnesium sulfate and stripped of solvents leaving a solid residue. The residue was recrystallized from an ether-pentane mixture to yield the desired product N-α-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2,6-diethylaniline having a melting point of 86° to 87°C.

Aufarbeitung

  1. customequipped with a mechanical stirrer
  2. additionwas added
  3. additionAfter the addition
  4. stirringwas completed stirring
  5. waitwas continued for a period of about 1 hour
  6. washthe resulting solution was washed with water
  7. dry with materialThe washed solution was then dried over anhydrous magnesium sulfate
  8. customleaving a solid residue
  9. customThe residue was recrystallized from an ether-pentane mixture

Quellen und Nachweise

ORD-Eintrag
ord-41d619f7a2b1498d93dba176783c7818
Quelldatensatz
uspto-grants-1976_02
Patentnummer
US03940259

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