Dichloroanilines

Pigment Red 144 [5280-784] 20735 disa2o condensation coupling of dia2oti2ed 2,5-dichloroaniline with 3-hydroxy-2-napthoic acid, foUowed by acid chloride formation and reaction with 2-chloro-/)-phen5iene- diamine... 

The principal use of (9-dichlorobenzene is to manufacture 3,4-dichloroaniline, which is a raw material for several herbicides and for the production of 3,4,4 -trichlorocarbaniHde (TCC), a bacteriostat used in deodorant soaps. Some is exported, but the amount is expected to decline as Brazil brings on increased capacity. A modest decline in U.S. consumption between 1989 and 1994 is expected. About 11,400 t were consumed in 1988. 

Vinclozolin sum of vinclozolin and all metabolites containing 3,5-dichloroaniline moeity, expressed as vinclozolin... 

D1CHLORO-5-PHENYL ISOCYANATE DICHLOROACETIC ACID DICHLOROACETYL CHLORIDE DICHLOROANILINE... 

A number of diarylmethyl alkylpiperazines, such as, for example lidoflazine, have found use as coronary vasodilators for the treatment of angina. The most recent of these interestingly incorporates a 2,6-dichloroaniline moiety reminiscent of antiarrhythmic agents. Treatment of the piperazine carboxamide 124 with acetone leads to formation of the nitrogen analogue of an acetal, the aminal 125. Alkylation of the remaining secondary nitrogen with chloroamide 126 leads to the intermediate 127. Exposure to aqueous acid leads to hydrolysis of the aminal function... 

N-(2,6-dichiorophenyl)thiourea (MP 149°C) was prepared in customary manner from 2,6-dichloroaniline (Organic Synthesis lil, 262-263) and ammonium thiocyanate. 16.0 g of this thiourea derivative were refiuxed for 2 A hours together with 16 g of methyl iodide in 150 cc of methanol. Thereafter, the methanol was evaporated out of the reaction mixture in vacuo, leaving as a residue 22 g of N-(2,6-dichlorophenyl)-S-methyl-isothiouronium hydroiodide of the formuia... 

N-Chloroacetyl-N-phenyl-2,6-dichloroaniline Aluminum chloride Sodium hydroxide... 

Four grams of N-chloroacetvl-N-phenvl-2,6-dichloroaniline and 4 grams of aluminum chloride are well mixed together and heated for 2 hours at 160°C. The melt is cooled and poured onto about 50 grams of Ice while it is still warm. The oil which separates is dissolved in 50 ml of chloroform, the chloroform solution is washed with 10 ml of water, dried over sodium sulfate and concentrated under 11 torr. The residue Is distilled. The 1-(2,6-dlchlorophenvD-2-indolinone melts at 126°-127°C. 

Dichloroaniline impurities aniline, chloroaniline, dichloro-aniline isomers, trichloroaniline isomers, tetrachloroaniline. tet-rachloroazobenzene, and pentachloroazobenzene... 

Fig. 1 Reflectance scan of a chromatogram track with 200 ng 2,3-dimethylaniline (1), 100 ng each of 4-chloro-2-methylamline (2), 3,4-dichloroaniline (3), 3,S-dichloroaniline (4) and 200 ng each of 2,3-dichloroaniline (S) and 2,S-dichloroaniline (6) per chromatogram zone.

Detection and result The chromatogram was dried (5 min in a stream of cold air), immersed in dipping solution I for 2 s and then dried in a stream of cold air. It was then immersed in dipping solution II for 1 s and dried in a stream of warm air for 5 min. Sulfanilic acid (h/ f 10-15), 4-isopropylanihne (h/ f 25-30), 4-chloroaniline (h/ f 40-45) and 3,4-dichloroaniline (h/ j 45-50) yielded pink-colored chromatogram zones on a colorless background. 

The detection limits lay between 20 ng (4-chloroaniline) and 80 ng (3,4-dichloroaniline) substance per chromatogram zone. 

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