2-bromo-5-chloro-4-methoxyaniline

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: To a solution of 0.60 g (2.54 mmol) 2-bromo-5-chloro-4-methoxy aniline and 0.88 ml (6.35 mmol) triethylamine in 20 ml chloroform was added 0.30 g (1.0 mmol) triphosgene at room temperature. The reaction mixture was stirred for 5 hours at r.t., then 0.47 g (3.0 mmol) 2-Amino-2-methyl-propionic acid methyl ester×HCl was added and the mixture was stirred at 60° C. overnight. The reaction was quenched with NaHCO3 solution, extracted into ethyl acetate. The organic phase was dried, evaporated and the product was purified by RP-HPLC to give 0.41 g (47%) of the desired hydantoin. the mixture was stirred at 60° C. overnight The reaction was quenched with NaHCO3 solution extracted into ethyl acetate The organic phase was dried evaporated the product was purified by RP-HPLC

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

Procedure: To a solution of 2.0 g (8.5 mmol) 2-bromo-5-chloro-4-methoxy aniline in 20 ml acetic acid and 20 ml water was added in small portions 1.37 g (17 mmol) potassium cyanate. The mixture was stirred at r.t. for 2 hours, neutralized with 2N NaOH and the product was extracted into ethyl acetate. Removal of the solvent and crystallization with ether gave 0.69 g (29%) of the desired urea. the product was extracted into ethyl acetate Removal of the solvent and crystallization with ether

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

Procedure: 4.40 g (18.6 mmol) 2-Bromo-5-chloro-4-methoxy-aniline and 3.1 ml (22.0 mmol) triethylamine were dissolved in 50 ml THF. 1.42 ml (20.0 mmol) acetylchloride were added dropwise at room temperature. The reaction mixture was stirred at room temperature for additional 2 hours, saturated NaHCO3 solution was added and the mixture was extracted with ethyl acetate. Removal of the solvent and crystallisation with ether gave 3.6 g (12.9 mmol, 69%) of the title compound. the mixture was extracted with ethyl acetate Removal of the solvent and crystallisation with ether