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With hydrogenchloride;copper(I) chloride; In water; acetic acid; sodium nitrite;
EXAMPLE 26 (2-Chloro-5-nitrophenyl)(2-chlorophenyl)methanone To 180 ml of concentrated sulfuric acid cooled to 0 in an ice bath was added 28 g (0.4 mol) of sodium nitrite in portions at such a rate that the temperature did not go above 10. This mixture was warmed on a steam bath until a solution formed. It was then cooled to 30 and a solution of 110.68 g (0.4 mol) of <strong>[2011-66-7]2-amino-5-nitro-2'-chlorobenzophenone</strong> in 300 mL of hot acetic acid was added at such a rate that the temperature did not exceed 40. This mixture was stirred without heating for 2.5 hr, and then poured slowly into a mixture of 800 mL of concentrated hydrochloric acid and 80 g of cuprous chloride. This mixture was heated to 80 on a steam bath for 40 min until the foaming had subsided, poured into 2 l of water, and allowed to stand overnight. The solid was collected, washed with water and recrystallized from methanol to give product, mp 76-79. An analytical sample prepared by recrystallization from methanol had mp 78.5-80.
With thionyl chloride; sodium hydrogencarbonate; In tetrahydrofuran; Petroleum ether;
(a) 53.6 g of carbobenzoxy-L-alanine are dissolved in 400 ml of dry tetrahydrofuran, the solution is treated dropwise with 30 g of thionyl chloride while cooling with ice and the mixture is stirred for 1 hour in the cold. A solution of 54 g (0.2 mol) of <strong>[2011-66-7]2-amino-5-nitro-2'-chlorobenzophenone</strong> in 150 ml of dry tetrahydrofuran is subsequently added dropwise thereto rapidly, whereupon the mixture is stirred at room temperature for 24 hours. The solution obtained is concentrated, the residue is treated with ice and 10 percent sodium bicarbonate solution and extracted with methylene chloride. The organic solution is dried over sodium sulphate and evaporated. The residue is treated with dry ether, left to crystallize for 1 hour and then filtered while rinsing with ether/petroleum ether (1:1). After drying, there is obtained (S)-benzyl-[1-[[2-(o-chlorobenzoyl)-4-nitrophenyl]carbamoyl]ethyl]carbamate of melting point 143-145; [alpha]25 D =18 (1 percent solution in methylene chloride).
(a) 100 g of <strong>[2011-66-7]2-amino-2'-chloro-5-nitrobenzophenone</strong> are suspended in 865 ml of 25% hydrochloric acid and treated portionwise with a total of 269 g of tin (II) chloride. The mixture is stirred at room temperature for 36 hours, then diluted with 0.5 l of an ice/water mixture and adjusted to pH 10 with about 2.17 l of a 28% sodium hydroxide solution. The mixture is extracted with methylene chloride. After evaporation of the solvent, the residue is dissolved in 0.54 l of ether and crystallized at about -20. There is obtained 2,5-diamino-2'-chlorobenzophenone of melting point 30-40.
2-amino-2'-chloro-5-nitrobenzophenone hydrazone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With hydrazine hydrate; In diethylene glycol;
Preparation 4 2-Amino-2'-chloro-5-nitrobenzophenone hydrazone In the manner given in Preparation 1, <strong>[2011-66-7]2-amino-2'-chloro-5-nitrobenzophenone</strong> is refluxed with hydrazine hydrate in diethylene glycol to give <strong>[2011-66-7]2-amino-2'-chloro-5-nitrobenzophenone</strong> hydrazone.
With phosphorus pentachloride; In tetrahydrofuran; toluene;
82 g of carbobenzoxy-L-alanine are dissolved in 100 ml of absolute tetrahydrofuran, the solution is cooled to -40 C and treated with 80 g of phosphorus pentachloride. The mixture is stirred at -30 C for 20 minutes and subsequently added to a shaken solution of 80 g of <strong>[2011-66-7]2-amino-5-nitro-2'-chlorobenzophenone</strong> in 100 ml of absolute tetrahydrofuran. The solution is concentrated on a rotary evaporator at 50-60 C, treated twice with toluene and evaporated each time. By crystallisation of the residue from ether, there is obtained (-)-benzyl-[1-[{2-(o-chlorobenzoyl)4-nitrophenyl}carbamoyl]-ethyl]carbamate which melts at 147 C and exhibits a rotation of [alpha]25D =-18.2 (in methylene chloride, 1%).
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