Chloroacetyl chloride → 2-Chloro-N-(4-ethylphenyl)-N-(2,3,5,6-tetrafluorophenyl)acetamide

HRID 603341Notes

Reaction equation

HRID 603341 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][CH:13]=1.[Cl:20][CH2:21][C:22](Cl)=[O:23].O1CCCC1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[N:11]([C:22](=[O:23])[CH2:21][Cl:20])[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 21938675N-(4-Ethylphenyl)-2,3,5,6-tetrafluoroaniline

Product 1

HCID 219386782-Chloro-N-(4-ethylphenyl)-N-(2,3,5,6-tetrafluorophenyl)acetamideYield 69.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

N-(2′,3′,5′,6′-tetrafluorophenyl)-4-ethylanilin (2.05 g) and chloro acetylchloride (1.99 g) is mixed without solvent and heated with stirring to 90° C. under nitrogen for 20 h. Tetrahydrofurane (10 ml) and aqueous sodium bicarbonate are added after cooling and stirring is continued for about 1 hour. The organic phase is diluted with toluene and washed with water three times and dried over magnesium sulfate. Evaporation and chromatography of the residue (silica, toluene) gave N-(2′,3′,5′,6′-tetrafluorophenyl)-N-chloroacetyl-4-ethylaniline (1.84 g) as a solid which is recrystallised from heptane, mp.: 72° C.

Workup

  1. temperatureheated
  2. temperatureafter cooling
  3. stirringstirring
  4. waitis continued for about 1 hour
  5. washwashed with water three times
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation and chromatography of the residue (silica, toluene)

Sources & evidence

ORD record
ord-1166832e05de4e5781426459d81b261c
Source dataset
uspto-grants-2011_03
Patent number
US07906677B2

Reaction notes

Loading…