Acetanilide, -chloroacetyl

The Friedel-Crafts acylation of acetanilide with chloroacetyl chloride yields l-acetamido-4-chloroacetylbenzene. The trimethylammonium group is introduced by reaction with trimethylamine, followed by hydrolysis of the acetamide group. This diazo component is a constituent of numerous yellow, orange, and red cationic azo dyes. Using diethyl- m-toluidine as the coupling component, the lightfast red dye 35 [67905-12-8] is obtained [99],... 

SYNS p-ACETAMIDOPHENACYL CHLORIDE p-(ACETYLAiMINO)PHENACYL CHLORIDE 4 -(CHLOROACETYL)ACETANILIDE NCI-C03770... 

CHLOROACETYL ACETANILIDE see CECOOO 4 -(CHLOROACETYL)ACETANILIDE see CECOOO N-(CHLOROACETYL)-3-AZABICYCLO(3.2.1)NONANE see CEClOO... 

In a 5-1. three-necked flask mounted on a steam bath in the hood and equipped with a mechanical stirrer (Note 1) and a wide-bore condenser (Note 1) is placed 1.4 kg. (I.l I.) of carbon disulfide. Through the open neck of the flask 202 g. (1.5 moles) of acetanilide and 300 g. (2.66 moles) of chloroacetyl chloride (Note 2) are introduced. The mixture is vigorously stirred while 600 g. (4.5 moles) of aluminum chloride is added in 25-50-g. portions over a period of 20-30 minutes the neck of the flask is stoppered between additions (Note 3). After the addition of the last portion of aluminum chloride, the mixture is heated at reflux temperature for 30 minutes while stirring is continued. Heating and stirring are discontinued and the mixture is allowed to stand for 3 hours, during which time it separates into layers. The upper layer (carbon disulfide) is decanted, and the viscous red-brown louder layer is poured cautiously with stirring into about 1 kg. of finely crushed ice to which 100 ml. of concentrated hydrochloric acid has been added. After the hydrolysis of the aluminum chloride, the product crystallizes as a white solid, which is collected on a Buchner funnel and washed well with water. It is then trans-... 

Boiling chloroacetyl chloride with pyrocatechol and phosphoryl chloride in benzene gives co-chloro-3,4-dihydroxyacetophenone in 85% yield.526 para-Acylation of acetanilide in 79-83% yield has been effected by chloroacetyl chloride and aluminum chloride in carbon disulfide.548... 

Qi) Acetanilide is a reactive substrate toward electrophilic aromatic substitution. On reaction with chloroacetyl chloride, it undergoes Friedel-Crafts acylation, primarily at its para position. 

Phenylalanine hydroxylase occurs only in mammalian liver (that is, in the rat, guinea-pig, rabbit, d<, chicken, and human) (see also 259). No activity has been observed in (rat) lung, kidney, brain, or muscle. The system is quite speciOc for L-phenylalanine. Tjrro-sine is not formed from n-phenylalanine, nor are the corresponding p-phenols formed from N-acetyl- or N-chloroacetyl-L-phenylalanine, L-phenylalanine ethyl ester, DL-phenylglycine, phenylserine, phenylpyruvic acid, phenylethylamine, benzoic acid, hippuric acid, cinnamic acid, or mandelic acid (768), or from aniline, acetanilide, tryptophan, kynurenine, anthranilic acid, or phenylacetate (557). This specificity is a distinguishing character of the enzyme, which occurs in the same tissue as the nonspecific aromatic hydroxylase described above. 

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