Sodium Iodide → 2-[2-(2,6-Dichloroanilino)phenyl]-N,N-dimethylacetamide

HRID 894397Notes

Reaction equation

HRID 894397 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].[CH3:10][N:11]([CH3:22])[C:12](=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1Br.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C1(C)C(C)=CC=CC=1.[Cu].O>[CH3:22][N:11]([CH3:10])[C:12](=[O:21])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=1[NH:4][C:3]1[C:2]([Cl:1])=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:9]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 118462,6-DichloroanilineHCID 128842292-(2-Bromophenyl)-N,N-dimethylacetamide

Product 1

HCID 128842302-[2-(2,6-Dichloroanilino)phenyl]-N,N-dimethylacetamide

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

In 80 ml of xylene (having a boiling point of 138° to 141° C.), 8.5 g (0.0525 mole) of 2,6-dichloroaniline was refluxed together with 5.2 g (0.0215 mole) of N,N-dimethyl-o-bromophenylacetamide, 5.0 g (0.0357 mole) of potassium carbonate, 1.0 g of copper powder, 1.0 g of cuprous iodide and 2.0 g of sodium iodide for 48 hours under agitation, while water formed by the reaction was being separated. After completion of the reaction, the reaction mixture was treated with active carbon while it was still warm, and the filtrate was concentrated. The obtained residue was mixed with methyl alcohol and the crystal precipitated on cooling was recovered by filtration, washed with methyl alcohol and dried.

Workup

  1. customformed by the reaction
  2. customwas being separated
  3. customAfter completion of the reaction
  4. additionthe reaction mixture was treated with active carbon while it
  5. temperaturewas still warm
  6. concentrationthe filtrate was concentrated
  7. additionThe obtained residue was mixed with methyl alcohol
  8. customthe crystal precipitated
  9. temperatureon cooling
  10. filtrationwas recovered by filtration
  11. washwashed with methyl alcohol
  12. customdried

Sources & evidence

ORD record
ord-fe076e463aa04bd58d29430088968f09
Source dataset
uspto-grants-1981_08
Patent number
US04283532

Reaction notes

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