2,6-Dimethylaniline → HCID 13014222, compound

HRID 1106213Notes

Reaction equation

HRID 1106213 reaction equation
[CH:1]1[C:6]([C:7]([CH2:9]Br)=[O:8])=[CH:5][CH:4]=[C:3]([Cl:11])[CH:2]=1.[CH3:12][C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:14]=1[NH2:15]>C(O)C>[CH3:12][C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:14]=1[NH:15][CH2:9][C:7](=[O:8])[C:6]1[CH:5]=[CH:4][C:3]([Cl:11])=[CH:2][CH:1]=1

Participants

4

Reactant 2

HCID 68962,6-DimethylanilineHCID 68303p-Chlorophenacyl bromide

Product 1

HCID 13014222HCID 13014222, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

46.7 g (0.2 mole) of ω-bromo-4-chloroacetophenone in 40 ml of ethanol were added to 48.4 g (0.4 mole) of 2,6-dimethylaniline in 40 ml of ethanol and the mixture was warmed to 50° C. for 20 minutes. Thereafter, it was cooled to 0° C. and the crystals which had formed were filtered off and rinsed with a little ethanol. 30 g (55% of theory) of 2,6-dimethyl-N-(4-chlorobenzoylmethyl)-aniline of melting point 82° C. were obtained.

Workup

  1. temperatureThereafter, it was cooled to 0° C.
  2. customthe crystals which had formed
  3. filtrationwere filtered off
  4. washrinsed with a little ethanol

Sources & evidence

ORD record
ord-d9b55057f8ef40a9a8cbf5b69133da8e
Source dataset
uspto-grants-1982_01
Patent number
US04312664

Reaction notes

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