2-Methoxy-5-sulfamoylbenzoic acid

2-Methoxy-5-sulfamoylbenzoic acid Structure
CAS No.
22117-85-7
Chemical Name:
2-Methoxy-5-sulfamoylbenzoic acid
Synonyms
Sulpride Impurity D;Sulpiride IMpurity D;Sulpiride EP Impurity D;Sulpiride Impurity D(EP);5-SulfaMoyl-o-anisic Acid;5-sulphamoyl-o-anisic acid;Levosulpiride - EP Impurity D;2-Methoxy-5-sulfamoylbenzoicaci;2-METHOXY-5-SULFONYLBENZOIC ACID;2-METHOXY-5-SULFAMOYLBENZOIC ACID
CBNumber:
CB7354418
Molecular Formula:
C8H9NO5S
Molecular Weight:
231.23
MOL File:
22117-85-7.mol
Modify Date:
2023/10/27 18:28:04

2-Methoxy-5-sulfamoylbenzoic acid Properties

Melting point 220 °C
Boiling point 482.5±55.0 °C(Predicted)
Density 1.492±0.06 g/cm3(Predicted)
storage temp. Room Temperature
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
pka 3.56±0.10(Predicted)
color White to Off-White
CAS DataBase Reference 22117-85-7(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36/37/39
Hazard Note  Irritant
HS Code  2922500090
NFPA 704
0
2 0

2-Methoxy-5-sulfamoylbenzoic acid Chemical Properties,Uses,Production

Uses

2-Methoxy-5-sulfamoylbenzoic Acid is a metabolite of the antipsychotic drug, Sulpiride (S689145).

Preparation

Synthesis of 2-methoxy-5-sulfamoyl benzoic Acid: In the amination reaction of 2-methoxyl-5-amino-sulfonyl benzoic acid, the main influence factors were mainly ammonia concentration, reaction temperature and reaction time. Firstly, we investigated two approaches of animation reaction: ventilation with ammonia in solvent and ammonium hydroxide as amino-reactant and solvent. In this section, the way of ventilation with ammonia in methyl alcohol and tetrahydrofuran would cause the rapid reaction, resulting to the incomplete reaction of 2-methoxy-5-sulfamoylbenzoic acid owing to the formation of 2-methoxy-5-sulfamoyl benzoic acid coated on the surface of the reaction. On the contrary, the lab test indicated that the way of ammonium hydroxide as amino-reactant and solvent can provide better experimental results. Secondly, the reactive temperature was the more important factor. The optimized amination temperature was to 30 °C. The low temperature would result to the long amination time, whereas high temperature can result to the generation of by-product owing to the hydrolysis of sulfonyl chloride. Finally, we evaluated the effect of reaction time. The optimized reaction time was to 5 hours. The extended reaction time can’t cause the significant improvement of yield. As a consequence, the best reactive temperature was to 30 °C and the best mole ratio between 2-methoxy-5-sulfonylchlorobenzoic acid and ammonium hydroxide was to 1:20 and the best reactive time was to 5 hours. Under the best conditions, the yield can reach to 75.8%.

2-Methoxy-5-sulfamoylbenzoic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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2-METHOXY-5-SULFAMOYLBENZOIC ACID 2-METHOXY-5-SULFONYLBENZOIC ACID 2-METHOXY-5-SULPHAMOYLBENZOIC ACID 3-CARBOXY-4-METHOXY-BENZENE SULFONAMIDE 2-Methoxy-5-Sufamoyl Benzoic Acid 5-Aminosulfonyl-2-Methoxybenzoic Acid 5-sulphamoyl-o-anisic acid 5-(Aminosulphonyl)-2-methoxybenzoic acid 2-METHOXY-5-SULFONAMIDOBENZOIC ACID 3-Carboxy-4-methoxybenzenesulphonamide 2-Methoxy-5-sulfaMidobenzoic Acid 5-SulfaMoyl-o-anisic Acid 2-METHOXY-5-SULFAMOYLBENZOIC ACIDSULPIRIDE Sulpiride IMpurity D 3-Carboxy-4-methoxybenzenesulphonamide, 5-(Aminosulphonyl)-o-anisic acid Benzoic acid,5-(aMinosulfonyl)-2-Methoxy- carbazole2-Methoxy-5-sulfamoylbenzoic acid Sulpiride Impurity D(EP) 6-methoxy-3-sulfonyl-1-cyclohexa-1,5-dienecarboxylic acid Sulpiride Impurity 4(Sulpiride EP Impurity D) Sulpiride EP Impurity D Levosulpiride - EP Impurity D 5-[(Aminoperoxy)thio]-2-methoxybenzoic Acid 2-Methoxy-5-sulfamoylbenzoicaci Sulpride Impurity D 22117-85-7 C8H8NO5S Organic acids Amines, Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds