| Identification | More | [Name]
4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid | [CAS]
71675-87-1 | [Synonyms]
2-METHOXY-4-AMINO-5-ETHYLSULFONYLBENZOIC ACID
4-AMINO-5-ETHANESULFONYL-2-METHOXY-BENZOIC ACID
4-AMINO-5-(ETHYLSULFONYL)-2-METHOXYBENZOIC ACID
4-Amino-5-(ethylsulphonyl)-o-anisic acid
2-methoxyl-4-amine-5-ethylsulfonylbenzoic acid
2-methoxy-4-amino-5-ethysulfonyl benzoic acid
2-METHOXY-4-AMINO-5-ETHYLSULFAMOYL BENZOIC ACID
BENZOICACID,4-AMINO-5-(ETHYLSULFONYL)-2-METHOXY
2-Methoxyl-4-amino-5-ethylsulfonylbenzoic acid | [EINECS(EC#)]
275-833-8 | [Molecular Formula]
C10H13NO5S | [MDL Number]
MFCD04973619 | [Molecular Weight]
259.28 | [MOL File]
71675-87-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Slightly Pink Solid | [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) |
| Hazard Information | Back Directory | [Chemical Properties]
Slightly Pink Solid | [Uses]
An impurity found in amisulpride (A633250). Amisulpride EP Impurity E | [Flammability and Explosibility]
Notclassified | [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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