Chloroacetyl chloride → N-(2',3',4',6'-tetrafluorophenyl)-N-chloroacetyl-4-methylaniline

HRID 603340Notes

Reaction equation

[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[C:4]([F:10])[C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.[Cl:19][CH2:20][C:21](Cl)=[O:22]>>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[C:4]([F:10])[C:3]=1[N:11]([C:21](=[O:22])[CH2:20][Cl:19])[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1

Participants

Reactant 2

HCID 6577Chloroacetyl chloride

HCID 579521482,3,4,6-Tetrafluoro-N-(4-methylphenyl)benzenamine

Product 1

HCID 57952153N-(2',3',4',6'-tetrafluorophenyl)-N-chloroacetyl-4-methylanilineYield 92.2%

Conditions

Temperature: 90 °C

Procedure

The mixture of N-(2′,3′,4′6′-tetrafluorophenyl)-4-methylanilin (0.82 g, 3.2 mmol) and chloro acetylchloride (1.6 g) is heated with stirring to 90° C. under nitrogen for 1.3 h. To destroy excess of the acid chloride, 2-propanol and water (2 ml each) is added and stirring is continued over night at room temperature. After adding toluene (20 ml), the mixture is extracted with sodium bicarbonate and the organic phase is dried with magnesium sulfate and evaporated to dryness. The residue is purified by flash chromatography (silica, toulene) to obtain N-(2′,3′,4′,6′-tetrafluorophenyl)-N-chloroacetyl-4-methylaniline (0.98 g, 2.95 mmol) as an oil.

Workup

temperatureis heated
customTo destroy excess of the acid chloride, 2-propanol and water (2 ml each)
additionis added
stirringstirring
waitis continued over night at room temperature
additionAfter adding toluene (20 ml)
extractionthe mixture is extracted with sodium bicarbonate
dry with materialthe organic phase is dried with magnesium sulfate
customevaporated to dryness
customThe residue is purified by flash chromatography (silica, toulene)

Sources & evidence

ORD record: ord-01a3f40045bc4e8e80d7a2f024dcea47
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906677B2

Reaction notes

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