4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid Chemical Properties

Melting point:

82-85°C

Boiling point:

529.6±50.0 °C(Predicted)

Density 

1.390±0.06 g/cm3(Predicted)

vapor pressure 

0Pa at 25℃

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

4.09±0.10(Predicted)

color 

White to buff coloured powder

Water Solubility 

8.555g/L at 25℃

InChI

InChI=1S/C10H13NO5S/c1-3-17(14,15)9-4-6(10(12)13)8(16-2)5-7(9)11/h4-5H,3,11H2,1-2H3,(H,12,13)

InChIKey

OJVNCXHGGYYOPH-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(S(CC)(=O)=O)=C(N)C=C1OC

LogP

0.46

CAS DataBase Reference

71675-87-1(CAS DataBase Reference)

Safety Information

HazardClass 

IRRITANT

HS Code 

29225090

4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid Usage And Synthesis

Chemical Properties

Slightly Pink Solid

Uses

An impurity found in amisulpride (A633250). Amisulpride EP Impurity E

Flammability and Explosibility

Not classified

Synthesis

The general procedure for the synthesis of 4-amino-5-(ethylsulfonyl)-2-methoxybenzoic acid using amisulpride impurity 4 as a starting material was as follows: 30% hydrogen peroxide was slowly added to isopropanol (4.84 L) at ambient temperature containing a catalytic amount of sodium tungstate (0.0082 kg) in 4-amino-2-methoxy-5-ethylthiomethyl benzoate (X) (1.21 kg) solution. The reaction mixture was stirred at 40-45 °C for 3-4 hours and subsequently cooled to 5-10 °C. To the reaction mixture, 5% sodium thiosulfate solution (0.06 kg dissolved in 18.15 L of water) was added and stirring was continued for 60 min to produce methyl 2-methoxy-4-amino-5-ethylsulfonylbenzoate (XI) in situ. Subsequently, sodium hydroxide (1.00 kg dissolved in 10 L of water) was added to the reaction mixture, warmed to 60-65 °C and stirred for 2-3 hours. Upon completion of the reaction, the reaction material was cooled and the pH was adjusted to 4.0-4.5 with dilute hydrochloric acid (1:10). the product was isolated by diafiltration in 82% yield and 99% purity.

References

[1] Patent: WO2011/158084, 2011, A1. Location in patent: Page/Page column 12
[2] Patent: WO2011/158084, 2011, A1

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