2,5-dichloroaniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using 5-chlorosalicylic acid and 2,5-dichloroaniline as the raw materials, the same operation as the example 16 gave the title compound.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound was prepared according to the procedure of Example 45, Step 1, using 4-amino-1,2,5-oxadiazole-3-carboxylic acid and 2,5-dichloroaniline as the starting materials. LCMS for C9H7Cl2N4O2 (M+H)+: m/z=273.0. This compound was prepared

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Triphenylphosphine (1.3 g) was added to a suspension of 2-[4-methyl-2-oxo-3-(thiophen-3-yl)-3-pyrrolin-1-yl]isobutyric acid (1 g) in carbon tetrachloride (9 mL) and dichloromethane (9 mL), and the mixture was heated at reflux for 30 minutes at 70° C. After ice-cooling the reaction solution, 2,5-dichloroaniline (0.61 g) and then triethylamine (0.38 g) were added, and the mixture was stirred for 24 hours at room temperature. After the reaction was completed, distilling off the solvent, water was added and the resulting mixture was extracted with ethyl acetate. The extract was washed with diluted hydrochloric acid and a saturated sodium hydrogencarbonate aqueous solution, and dried over anhydrous sodium sulfate. After distilling off ethyl acetate, the resulting crude product was purified by preparative thin-layer chromatography (developing solvent: chloroform/ethyl acetate=20/1) to give 0.35 g of the title compound. the mixture was heated distilling off the solvent, water was added the resulting mixture was extracted with ethyl acetate The extract was washed with diluted hydrochloric acid a saturated sodium hydrogencarbonate aqueous solution, and dried over anhydrous sodium sulfate After distilling off ethyl acetate the resulting crude product was purified by preparative thin-layer chromatography (developing solvent: chloroform/ethyl acetate=20/1)

Conditions: temp:-1.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 500 ml flask under a nitrogen atmosphere, concentrated HCl (180 ml, 32%, 10.17 M, 1.83 moles) was charged and cooled down to −2 to 0° C. 2,5-Dichloroaniline (30 g, 185 mmoles) was added in one portion as a solid. The acidic suspension was re-cooled to −2 to 0° C. and sodium nitrite (15.3 g, 222 mmoles) dissolved in water (30 ml) was added dropwise to the acidic mixture through an addition funnel over a period of 1 hour at −2 to 0° C. The resulting mixture was kept with stirring for 1 hour at −2 to 0° C. Next, L-ascorbic acid (34.2 g, 194 mmoles) was added portionwise as a solid at −2 to 0° C. The reaction mixture was allowed to come to room temperature (18-20° C.). A thick orange suspension was formed. The reaction mixture was diluted with concentrated HCl (50 ml, 32%, 0.51 moles, 2.7 eq) and water (150 ml) and then filtered. The wet solid was triturated in water (650 ml) at 20-25° C. for 16 hours, filtered, washed with water and dried to constant weight to afford 34 g of crude oxalic acid derivative as a red crystalline solid. The acidic suspension was re-cooled to −2 to 0° C. was added dropwise to the acidic mixture through an addition funnel over a period of 1 hour at −2 to 0° C to come to room temperature (18-20° C.) A thick orange suspension was formed filtered The wet solid was triturated in water (650 ml) at 20-25° C. for 16 hours filtered washed with water dried to constant weight

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,4-Dichloropyrimidine (50 g, 0.34 mol), 2,5-dichloroaniline (54.38 g, 0.34 mol) and concentrated hydrochloric acid (cat. amount) were dissolved in n-butanol (250 ml). The reaction mixture was stirred at room temperature for 12 hours after which the solid that had formed was collected by filtration. The organics were allowed to stand for 48 hours and the solid that formed was collected by filtration, washed with EtOAc and dried to give the title product as a white solid (18.65 g). NMR (300 MHz): 6.82 (d, 1H), 7.31 (dd, 1H), 7.58 (d, 1H), 7.82 (s, 1H), 8.19 (d, 1H), 9.82 (s, 1H); m/z: (ES+) 273.9 (MH+). that had formed was collected by filtration to stand for 48 hours the solid that formed was collected by filtration washed with EtOAc dried

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In the manner described in example 3, 2-bromophenylacetic acid was condensed with 2,5-dichloroaniline to yield 2-[(2,5-dichlorophenyl)amino]phenylacetic acid.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In the manner described in example 3, 2-bromophenylacetic acid was condensed with 2,5-dichloroaniline to yield 2-[(2,5-dichlorophenyl)amino]phenylacetic acid.

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 16.1 g (0.1 mole) of 2,5-dichloroaniline was dissolved in a mixed solution of 85 ml of concentrated hydrochloric acid and 200 ml of water while stirring with heating on a water bath and the solution was cooled to 5° C and a solution prepared by dissolving 8.28 g (0.12 mole) of sodium nitrite in 50 ml of water was slowly added dropwise. The temperature was kept at 5° C and after completion of the addition of the solution was stirred for 20 minutes, sulfamic acid was added thereto to decompose excess HNO2. Thereafter, the solution was filtered and added at a time to a solution prepared by dissolving 23.6 g (0.1 mole) of N-[β-(β-ethoxy)ethoxy]ethyl-N-ethylaniline in 1 l of 1N-HCl. Furthermore, about 500 ml of water was added thereto and with stirring about 200 g of sodium acetate were added thereto. After allowing to stand for several hours, it was filtered and the azo dye which adhered to wall of device and filter paper was collected and used for the next reaction without purification. The crude product was 34.1 g. with heating on a water bath a solution prepared was slowly added dropwise was kept at 5° C after completion of the addition of the solution was stirred for 20 minutes Thereafter, the solution was filtered added at a time to a solution prepared were added to stand for several hours it was filtered filter paper was collected used for the next reaction without purification