Chloroacetyl chloride → N-(2',6'-dichlorophenyl)-N-chloroacetyl-4-methylaniline

HRID 603348

Reaction equation

HRID 603348 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1.[Cl:17][CH2:18][C:19](Cl)=[O:20]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]([C:19](=[O:20])[CH2:18][Cl:17])[C:10]1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 57952151N-(2',6'-Dichlorophenyl)-4-methylaniline

Product 1

HCID 57952147N-(2',6'-dichlorophenyl)-N-chloroacetyl-4-methylaniline

Procedure

N-(2′,6′-Dichlorophenyl)-4-methylaniline (4.86 g) is reacted with chloroacetylchloride (3.92 g) at 90° C. for 2 h. After dilution with toluene, the mixture is washed with aqueous sodiumcarbonate twice, 40% aqu. sodium bisulfite and water. The organic phase is dried (MgSO4) and evaporated. The residue is recrystallised from ethanol (12 g) to obtain N-(2′,6′-Dichlorophenyl)-N-chloroacetyl (2.83 g), mp: 129.5-130° C.

Workup

  1. washAfter dilution with toluene, the mixture is washed with aqueous sodiumcarbonate twice
  2. dry with materialThe organic phase is dried (MgSO4)
  3. customevaporated
  4. customThe residue is recrystallised from ethanol (12 g)
  5. customto obtain N-(2′,6′-Dichlorophenyl)-N-chloroacetyl (2.83 g), mp: 129.5-130° C.

Sources & evidence

ORD record
ord-956fed54a7fb4ecaa4fe37157e1534b6
Source dataset
uspto-grants-2011_03
Patent number
US07906677B2

Linked notes

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