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

HRID 267463Notes

Reaction equation

HRID 267463 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][NH:8][C:9]1[C:14]([CH2:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:17][CH3:18].C(=O)(O)[O-].[Na+].O1CCOCC1.[Cl:30][CH2:31][C:32](Cl)=[O:33]>CCOCC.O>[Cl:30][CH2:31][C:32]([N:8]([CH2:7][CH:2]1[O:3][CH2:4][CH2:5][CH2:6][O:1]1)[C:9]1[C:14]([CH2:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:17][CH3:18])=[O:33]

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 21548994HCID 21548994, compound

Product 1

HCID 198266112-Chloro-N-(2,6-diethylphenyl)-N-[(1,3-dioxan-2-yl)methyl]acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

N-(1,3-Dioxan-2-ylmethyl)-2,6-diethylaniline (25 grams), sodium bicarbonate (10 grams), dioxane (30 ml) and water (4 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The mixture is cooled to a temperature of about 0°C and chloroacetyl chloride (15 grams) is added, with stirring, over a period of about 15 minutes. After the addition is completed stirring is continued for a period of about 1 hour. After this time ether (100 ml) is added to the mixture and the resulting solution is washed with water. The washed solution is then dried over anhydrous magnesium sulfate and stripped of solvents leaving a solid residue. The residue is recrystallized to yield the desired product N-α-chloroacetyl-N-(1,3-dioxan-2-ylmethyl)-2,6-diethylaniline.

Workup

  1. customequipped with a mechanical stirrer
  2. additionis added
  3. additionAfter the addition
  4. stirringis completed stirring
  5. waitis continued for a period of about 1 hour
  6. washthe resulting solution is washed with water
  7. dry with materialThe washed solution is then dried over anhydrous magnesium sulfate
  8. customleaving a solid residue
  9. customThe residue is recrystallized

Sources & evidence

ORD record
ord-faffc4f00f8a451893559f1ed09c42e7
Source dataset
uspto-grants-1976_03
Patent number
US03942972

Reaction notes

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