4-Chloro-2-toluidine → HCID 178456755, compound

HRID 2052367

Reaction equation

[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][CH2:6][N-:7][CH2:8][CH2:9][CH3:10].O=P(Cl)(Cl)Cl.[Cl:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[C:24]([CH3:29])[CH:23]=1.[OH-].[Na+].O>ClCCCl>[Cl:21][C:22]1[CH:28]=[CH:27][C:25]([N:26]=[C:8]([NH:7][CH2:6][CH2:5][O:4][C:3]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:2]=2[Cl:1])[CH2:9][CH3:10])=[C:24]([CH3:29])[CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 19.5 g (0.075 mole) of N-(2-(2,4-dichlorophenoxy)ethyl)propylamide, 11.4 g (0.075 mole) POCl3 and 250 mls of 1,2-dichloroethane was stirred at 60° C. for six hours. The mixture was cooled to 25° C., whereupon 10.4 g (0.075 mole) of 4-chloro-2-methylaniline was added thereto. An exotherm was noted. The mixture was refluxed for 10 hours and allowed to cool. The product mixture was made basic with a 20% NaOH water solution. The product layer was separated, washed once with 200 ml of water, dried over sodium sulfate, filtered and distilled under reduced pressure to give 65% yield (based on the amide) of the desired product, a thick oil, b.p. 142° C./1.3 mm Hg . NMR confirmed the assigned structure: ##STR4##

Workup

additionwas added
temperatureThe mixture was refluxed for 10 hours
temperatureto cool
customThe product layer was separated
washwashed once with 200 ml of water
dry with materialdried over sodium sulfate
filtrationfiltered
distillationdistilled under reduced pressure
customto give 65% yield (

Sources & evidence

ORD record: ord-8a8c22dcdc1e4b128b1c1a633f1bde0f
Source dataset: uspto-grants-1980_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04183957

Linked notes

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