Chloroacetyl chloride → N-alpha-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2,6-dimethylaniline

HRID 1578908Notes

Reaction equation

HRID 1578908 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:15].C(=O)(O)[O-].[Na+].O1CCOCC1.[Cl:27][CH2:28][C:29](Cl)=[O:30]>CCOCC.O>[Cl:27][CH2:28][C:29]([N:7]([CH2:6][CH:2]1[O:3][CH2:4][CH2:5][O:1]1)[C:8]1[C:9]([CH3:15])=[CH:10][CH:11]=[CH:12][C:13]=1[CH3:14])=[O:30]

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 312751,4-DioxaneHCID 1047101,3-Dioxolane-2-methanamine, N-(2,6-dimethylphenyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 13017584N-alpha-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2,6-dimethylaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

N-(1,3-Dioxolan-2-ylmethyl)-2,6-dimethylaniline (7.8 grams), sodium bicarbonate (7.0 grams), dioxane (20 ml) and water (4 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The mixture was cooled to a temperature of about 0°C and chloroacetyl chloride (5.0 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-dimethylaniline having a melting point of 58° to 60°C.

Workup

  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

Sources & evidence

ORD record
ord-e5ab9ae338f948f89ac1657d2c672193
Source dataset
uspto-grants-1976_02
Patent number
US03940259

Reaction notes

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