Benzoic acid, 5-chloro-2-nitro-, methyl ester

white to light yellow crystalline powder or chunks

This example concerns the synthesis of Methyl ester 80: To a stirred solution of 9 (9.393 g, 46.60 mmol) in dry DMF (155 mL) at 0Example14:1 (Procedure R)2-(4-Chloro-phenylamino)-5-r4-(4-chlorophenylamino)phenylsulfanvnbenzoic acidStep 1 : Methyl 5-chloro-2-nitrobenzoateDimethyl sulfate (15 ml_, 150 mmol) was added dropwise to a mixture of 5-chloro-2-nitro benzoic acid (20 g, 100 mmol), NaReference 5-Chloro-2-nitro-benzoic acid (compound A') (5.0 g) was dissolved in methanol (150 ml). Thionyl chloride (9.5 ml) was added to the solution at 0°C, and the mixture was heated under reflux with stirring for 15 hr. After the completion of the reaction, distilled water was added thereto at 0°C, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with distilled water and saturated brine, was dried over sodium sulfate, and was then concentrated to give 5-chloro-2-nitro-benzoic acid methyl ester as a useful intermediate (12.9 g, yield 92percent).Example14:1 (Procedure R)2-(4-Chloro-phenylamino)-5-r4-(4-chlorophenylamino)phenylsulfanvnbenzoic acidStep 1 : Methyl 5-chloro-2-nitrobenzoateDimethyl sulfate (15 ml_, 150 mmol) was added dropwise to a mixture of 5-chloro-2-nitro benzoic acid (20 g, 100 mmol), Na2CO3 (15.9 g, 150 mmol) in acetone.The mixture was heated at rx for 3 h, cooled, filtered and concentrated. Extractive workup (EtOAc, water, brine), drying (Na2SO4) gave a solution from which the sub-title compound was obtained as a solid after addition of a small amount of petroleum ether and standing in the cold. Yield: 16.9 g (78percent).Reference :Preparation of Reference Preparation of Methyl 5-chloro-2-nitrobenzoate Potassium carbonate (515 gm) was added to a solution of 5-chloro-2-nitro benzoic acid (500 gm) in acetone (2750 ml) at room temperature. Dimethyl sulphate (306.5 gm) was added to the reaction mixture slowly and heated to reflux for 30 minutes. The reaction mass was filtered and then concentrated to obtain a residual mass. The residual mass was poured to the ice water and extracted with methylene chloride. The solvent was distilled off under reduced pressure to obtain a residual solid of Reference Preparation of methyl 2-amino-5-chlorobenzoateA mixture of Reference Preparation of Methyl 2-amino-5-chlorobenzoate A mixture of

Molecular Weight:215.59
XLogP3:2.5
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:214.9985354
Monoisotopic Mass:214.9985354
Topological Polar Surface Area:72.1
Heavy Atom Count:14
Complexity:240
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes