Benzene → HCID 21403907, compound

HRID 268045Notes

Reaction equation

HRID 268045 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]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:16].C(=O)([O-])[O-].[Na+].[Na+].C1C=CC=CC=1.[Cl:29][CH2:30][C:31](Cl)=[O:32]>CCOCC.O>[Cl:29][CH2:30][C:31]([N:8]([CH2:7][CH:2]1[O:3][CH2:4][CH2:5][CH2:6][O:1]1)[C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:16])=[O:32]

Participants

7

Reactant 4

HCID 241BenzeneHCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 21419811HCID 21419811, compound

Product 1

HCID 21403907HCID 21403907, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

N-(1,3-Dioxan-2-ylmethyl)-2,6-dimethylaniline prepared in Example 2 (5 grams), sodium carbonate (3 grams), benzene (30 ml) and water (30 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The mixture was cooled to a temperature of from about 0° to about 5°C and chloroacetyl chloride (2.8 grams) was slowly added over a period of about 15 minutes. After the addition was completed stirring was continued at room temperature for a period of about one hour. Ether (100 ml) was then added to the reaction mixture and the resulting solution was washed with water. The washed solution was dried over anhydrous magnesium sulfate and stripped of solvents leaving a solid residue. The residue was recrystallized from heptane to yield the desired product N-α-chloroacetyl-N-(1,3-dioxan-2-ylmethyl)-2,6-dimethylaniline having a melting point of 100° to 102°C.

Workup

  1. customequipped with a mechanical stirrer
  2. additionwas slowly added over a period of about 15 minutes
  3. additionAfter the addition
  4. washthe resulting solution was washed with water
  5. dry with materialThe washed solution was dried over anhydrous magnesium sulfate
  6. customleaving a solid residue
  7. customThe residue was recrystallized from heptane

Sources & evidence

ORD record
ord-6473dc81fa8a4c0fb411414ecb7408a8
Source dataset
uspto-grants-1976_03
Patent number
US03946043

Reaction notes

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