2-ethoxybenzoyl chloride

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

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

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

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

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: The title compound was prepared from 2-amino-3-carbamoylbenzamide and 2-ethoxybenzoyl chloride following the procedure of Preparation 5 and was obtained as colourless crystals (33%), m.p. 224-225° C. the procedure of Preparation 5

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

Procedure: The title compound was prepared from 2-amino-3-methylbenzamide (Chem. Pharm. Bull., 1988, 36, 2955) and 2-ethoxybenzoyl chloride following the procedure of Preparation 5 and was obtained as colourless crystals (71%), m.p. 197-200° C. the procedure of Preparation 5

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

Procedure: A mixture of 2-amino-6-methylbenzamide (UK Patent Application No 1,276,359; 5.49 g, 0.0365 mol), 2-ethoxybenzoyl chloride (7.67 g, 0.0415 mol) and pyridine (100 ml) was stirred at room temperature for 20 hours. The solvent was then removed by evaporation under vacuum and the residue dissolved in dichioromethane (200 ml). The solution was washed with saturated aqueous sodium carbonate solution (200 ml) and the aqueous phase back-extracted with further dichioromethane (2×100 ml). The organic solutions were combined, washed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml), then dried (Na2SO4) and evaporated under vacuum to give the title compound, which recrystallized from ethyl acetate as a colourless solid (6.86g, 63%), m.p. 166-168° C. The solvent was then removed by evaporation under vacuum the residue dissolved in dichioromethane (200 ml) The solution was washed with saturated aqueous sodium carbonate solution (200 ml) the aqueous phase back-extracted with further dichioromethane (2×100 ml) washed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml) dried (Na2SO4) evaporated under vacuum

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

Procedure: 2-Ethoxybenzoyl chloride (8.9 g, 0.048 mol) was added dropwise to a stirred solution of 2-amino-3-methoxybenzamide (4.0 g, 0.024 mol) in pyridine (35 ml) under a nitrogen atmosphere at 0° C. After 20 hours at room temperature, the solvent was removed by evaporation under vacuum, the residue dissolved in dichloromethane (100 ml) and the solution washed successively with 2N hydrochloric acid (2×100 ml) and saturated aqueous sodium hydrogen carbonate solution (2×100 ml). The organic phase was dried (MgSO4) and evaporated under vacuum, then the resulting oil chromatographed on silica gel (40 g), eluting with a mixture of methanol in-dichloromethane (2%), to give the title compound as a colourless solid (4.1 g, 54%), m.p. 177-179° C. the solvent was removed by evaporation under vacuum the residue dissolved in dichloromethane (100 ml) the solution washed successively with 2N hydrochloric acid (2×100 ml) and saturated aqueous sodium hydrogen carbonate solution (2×100 ml) The organic phase was dried (MgSO4) evaporated under vacuum the resulting oil chromatographed on silica gel (40 g) eluting with a mixture of methanol in-dichloromethane (2%)

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

Procedure: The title compound was prepared from 2-amino-3-carbamoylbenzamide and 2-ethoxybenzoyl chloride following the procedure of Preparation 5 and was obtained as colorless crystals (33%), m.p. 224°-225° C. Found: C,62.57; H,5.18; N,12.81. C17H17N3O4 requires C,62.37; H,5.24; N,12.84%. the procedure of Preparation 5

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

Procedure: The title compound was prepared from 2-amino-3-methylbenzamide (Chem. Pharm. Bull., 1988, 36, 2955) and 2-ethoxybenzoyl chloride following the procedure of Preparation 5 and was obtained as colorless crystals (71%), m.p. 197°-200° C. Found: C,68.80; H,5.99; N,9.36. C17H18N2O3 requires C,68.44; H,6.08; N,9.39%. the procedure of Preparation 5