Chloroacetyl chloride → N-(2'-Chloro-6'-methylphenyl)-N-chloroacetyl-4-methylaniline

HRID 603343

Reaction equation

HRID 603343 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[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]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]([C:19](=[O:20])[CH2:18][Cl:17])[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 57952145N-(2'-chloro-6'-methylphenyl)-4-methylaniline

Product 1

HCID 57952152N-(2'-Chloro-6'-methylphenyl)-N-chloroacetyl-4-methylanilineYield 77.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The solution of N-(2′-chloro-6′-methylphenyl)-4-methylaniline (1.4 g) in 2.21 g chloroacetylchloride is heated to 90° C. for 4 h. The mixture is diluted with toluene (25 ml), cooled to room temperature and washed with aqu. sodium carbonate. The organic phase is dried, evaporated and the residue is subjected to flash chromatography [57 g silica, toluene and toluene/ethylacetate (98:2)] to afford 1.45 g of N-(2′-Chloro-6′-methylphenyl)-N-chloroacetyl-4-methylaniline which is crystallised from heptane, mp: 113-114° C.

Workup

  1. washwashed with aqu
  2. customThe organic phase is dried
  3. customevaporated

Sources & evidence

ORD record
ord-a3456b5d6a45462da116fb640b9a79d2
Source dataset
uspto-grants-2011_03
Patent number
US07906677B2

Linked notes

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