Chloroacetyl chloride → 2-chloro-N-(2-chloro-6-fluorophenyl)-N-(4-methylphenyl)acetamide

HRID 1242256

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F: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].CCCCC>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F: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

Conditions

Temperature: -15 °C

Procedure

A mixture of 25 g (0.11 mol) N-(2′-chloro-6′-fluorophenyl)-4-methylaniline and 40 ml (0.5 mol) of chloroacetylchloride is heated under a nitrogen atmosphere for 15 minutes at 60°. The solvent is evaporated under reduced pressure to give an oil which is dissolved in 25 ml of ethyl acetate. Pentane (250 ml) is added dropwise over 15 minutes to precipitate the product. The mixture is cooled to −15° C. and the solid is filtered and washed with pentane to give N-(2′-chloro-6′-fluorophenyl)-N-chloroacetyl-4-methylaniline, m.p. 80–83°.

Workup

temperatureis heated under a nitrogen atmosphere for 15 minutes at 60°
customThe solvent is evaporated under reduced pressure
customto give an oil which
customto precipitate the product
filtrationthe solid is filtered
washwashed with pentane

Sources & evidence

ORD record: ord-94074bad72a84be8b1d96a8a12ba9b93
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115662B2

Linked notes

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