| Identification | More | [Name]
2-Methoxy-5-sulfamoylbenzoic acid | [CAS]
22117-85-7 | [Synonyms]
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
2-METHOXY-5-SULFAMOYLBENZOIC ACIDSULPIRIDE | [EINECS(EC#)]
244-789-1 | [Molecular Formula]
C8H9NO5S | [MDL Number]
MFCD00129997 | [Molecular Weight]
231.23 | [MOL File]
22117-85-7.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [Hazard Note ]
Irritant | [HS Code ]
2922500090 |
| Hazard Information | Back Directory | [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%. |
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