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24683-26-9

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Basic Information
CAS No.: 24683-26-9
Name: Ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
Article Data: 7
Molecular Structure:
Molecular Structure of 24683-26-9 (Ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide)
Formula: C12H13 N O5 S
Molecular Weight: 283.305
Synonyms: 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylicacid ethyl ester 1,1-dioxide; Ethyl4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
EINECS: 246-403-7
Density: 1.444g/cm3
Melting Point: 140-144 ºC
Boiling Point: 424.1°Cat760mmHg
Flash Point: 210.3°C
Appearance: White to Off-White Solid
Hazard Symbols:
Risk Codes: R23   
Safety: Low toxicity by ingestion and inhalation. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NOx and SOx.
Transport Information: UN 2811
PSA: 92.29000
LogP: 2.12910
Related products
Synthetic route
24683-21-4

4-hydroxy-2H-1,2-benzothiazine-3-carboxylic acid ethyl ester 1,1-dioxide

77-78-1

dimethyl sulfate

24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Conditions
ConditionsYield
With hydrogenchloride In water at 10℃; for 18h; pH=7.5;78.9%
113412-08-1

2-(Ethoxycarbonylmethyl-methyl-sulfamoyl)-benzoic acid ethyl ester

24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 5.5h;76%
24683-21-4

4-hydroxy-2H-1,2-benzothiazine-3-carboxylic acid ethyl ester 1,1-dioxide

74-88-4

methyl iodide

24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 20℃; for 18h;72%
With sodium methylate In N,N-dimethyl-formamide
With sodium hydroxide In ethanol; water at 20℃; for 24h;
24683-20-3

ethyl 2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl) acetate

24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 68 percent / EtONa / ethanol / 1 h / 55 °C
2: 72 percent / aq. NaOH / ethanol / 18 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 1) NaOEt / 1) room temperature, 7-10 min.; 2) room temperature, 2 h
2: 76 percent / lithium diisopropylamide / tetrahydrofuran / 5.5 h / -78 °C
View Scheme
Multi-step reaction with 2 steps
1: NaOEt / ethanol
2: NaOMe / dimethylformamide
View Scheme
Multi-step reaction with 2 steps
1: sodium methylate / dimethyl sulfoxide / 1 h / 30 °C
2: sodium hydroxide / water; ethanol / 24 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride; sodium / ethanol / 0.5 h / 70 °C / pH 8 - 9
2: hydrogenchloride / water / 18 h / 10 °C / pH 7.5
View Scheme
128-44-9

saccharin sodium salt

24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 72 percent / dimethylformamide / 3 h / 100 °C
2: 68 percent / EtONa / ethanol / 1 h / 55 °C
3: 72 percent / aq. NaOH / ethanol / 18 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 3 h / 75 °C
2: hydrogenchloride; sodium / ethanol / 0.5 h / 70 °C / pH 8 - 9
3: hydrogenchloride / water / 18 h / 10 °C / pH 7.5
View Scheme
24683-21-4

4-hydroxy-2H-1,2-benzothiazine-3-carboxylic acid ethyl ester 1,1-dioxide

methyl halide

methyl halide

24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Conditions
ConditionsYield
Stage #1: 4-hydroxy-2H-1,2-benzothiazine-3-carboxylic acid ethyl ester 1,1-dioxide With sodium hydroxide In ethanol; water
Stage #2: methyl halide In ethanol; water at 20℃; for 12h;
81-07-2

saccharin

24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydride / N,N-dimethyl-formamide / 3.5 h / 80 °C / Cooling with ice
2: sodium methylate / dimethyl sulfoxide / 1 h / 30 °C
3: sodium hydroxide / water; ethanol / 24 h / 20 °C
View Scheme
7305-71-7

5-methyl-2-thiazol-2-amine

24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

71125-38-7

meloxicam

Conditions
ConditionsYield
In o-xylene for 24h; Product distribution / selectivity; Heating / reflux;95%
In xylene at 139 - 140℃; for 32 - 37h; Product distribution / selectivity; Heating / reflux; Molecular sieve;92.48%
358-23-6

trifluoromethylsulfonic anhydride

24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

C13H12F3NO7S2

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 24.1667h;92%
With pyridine In dichloromethane
7305-71-7

5-methyl-2-thiazol-2-amine

24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

95-50-1

1,2-dichloro-benzene

71125-38-7

meloxicam

Conditions
ConditionsYield
With 1,2-dichloro-ethane76%
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Chemistry

Empirical Formula: C12H13NO5S
Molecular Weight: 283.3003 
EINECS: 246-403-7 
Index of Refraction: 1.617
Density: 1.458 g/cm3
Flash Point: 224.8 °C
Enthalpy of Vaporization: 74.46 kJ/mol
Boiling Point: 448.1 °C at 760 mmHg
Vapour Pressure: 8.16E-09 mmHg at 25 °C
Melting point: 140-144 °C(lit.)
Appearance: White to off-white solid
Product categories of Ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (CAS NO.24683-26-9): Organic acids;API intermediates;Aromatics Compounds;Heterocycles;Heterocyclic Building Blocks;Thiazines
Structure of Ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (CAS NO.24683-26-9):
                    

Uses

 Ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (CAS NO.24683-26-9) can be used for piroxicam (Yan Tong Xi Kang) intermediate.

Toxicity Data With Reference

1.    

orl-rat LD50:4800 mg/kg

     MTPEEI    Meditsina Truda i Promyshlennaya Ekologiya. Industrial Medicine and Ecology.(11),(1996),45.
2.    

ihl-rat LC50:1562 mg/m3

     MTPEEI    Meditsina Truda i Promyshlennaya Ekologiya. Industrial Medicine and Ecology.(11),(1996),45.
3.    

orl-gpg LD50:5300 mg/kg

     MTPEEI    Meditsina Truda i Promyshlennaya Ekologiya. Industrial Medicine and Ecology.(11),(1996),45.

Safety Profile

Low toxicity by ingestion and inhalation. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NOx and SOx.
 

Hazard Codes: ToxicT
Risk Statements: 23 
R23 :Toxic by inhalation.
Safety Statements: 45 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

Specification

 Ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide ,its cas register number is 24683-26-9. It also can be called Ethyl 4-hydroxy-2-methyl-1,1-dioxo-2H-1,2-benzothiazine-3-carboxylate and 2H-1,2-Benzothiazine-3-carboxylic acid, 4-hydroxy-2-methyl-, ethyl ester, 1,1-dioxide .