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Basic Information
CAS No.: 123663-49-0
Name: Iguratimod
Molecular Structure:
Molecular Structure of 123663-49-0 (Iguratimod)
Formula: C17H14N2O6S
Molecular Weight: 374.374
Synonyms: T 614;T614 (antiinflammatory);Ailamode;3-Formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one;N-[3-(Formylamino)-4-oxo-6-phenoxy-4H-chromen-7-yl]methanesulfonamide;
EINECS: 808-127-0
Density: 1.52 g/cm3
Melting Point: 238.0 to 242.0 °C
Boiling Point: 580.6 °C at 760 mmHg
Flash Point: 304.9 °C
Appearance: white powder
PSA: 123.09000
LogP: 4.38780
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Synthetic route
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N,N-dimethyl-formamide dimethyl acetal

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α-formamido-2'-hydroxy-4'-methanesulfonamido-5'-phenoxyacetophenone

123663-49-0

Iguratimod

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 15℃; for 8h; Cyclization;87%
2258-42-6

Acetic formic anhydride

123663-48-9

N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)methanesulfonamide

123663-49-0

Iguratimod

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h; Formylation;73%
123663-48-9

N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)methanesulfonamide

123663-49-0

Iguratimod

Conditions
ConditionsYield
With formic acid; acetic anhydride In dichloromethane; di-isopropyl ether73%
84594-95-6

4-methoxy-2-nitro-1-phenoxybenzene

123663-49-0

Iguratimod

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C
2: 82 percent / pyridine / 1 h / 20 °C
3: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C
4: 91 percent / acetone / 3 h
5: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C
6: 87 percent / dimethylformamide / 8 h / 15 °C
View Scheme
Multi-step reaction with 9 steps
1: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C
2: 82 percent / pyridine / 1 h / 20 °C
3: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C
4: 70 percent aq. HClO4 / 1 h / 20 °C
5: H2O / 0.08 h / Heating
6: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr
7: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C
8: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C
9: 73 percent / CH2Cl2 / 1 h / 20 °C
View Scheme
76838-72-7

5-methoxy-2-phenoxyaniline

123663-49-0

Iguratimod

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 82 percent / pyridine / 1 h / 20 °C
2: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C
3: 91 percent / acetone / 3 h
4: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C
5: 87 percent / dimethylformamide / 8 h / 15 °C
View Scheme
Multi-step reaction with 8 steps
1: 82 percent / pyridine / 1 h / 20 °C
2: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C
3: 70 percent aq. HClO4 / 1 h / 20 °C
4: H2O / 0.08 h / Heating
5: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr
6: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C
7: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C
8: 73 percent / CH2Cl2 / 1 h / 20 °C
View Scheme
10298-80-3

2-chloro-5-methoxynitrobenzene

123663-49-0

Iguratimod

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 84 percent / potassium tert-butoxide / dimethylformamide / 4 h / 110 °C
2: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C
3: 82 percent / pyridine / 1 h / 20 °C
4: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C
5: 91 percent / acetone / 3 h
6: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C
7: 87 percent / dimethylformamide / 8 h / 15 °C
View Scheme
Multi-step reaction with 10 steps
1: 84 percent / potassium tert-butoxide / dimethylformamide / 4 h / 110 °C
2: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C
3: 82 percent / pyridine / 1 h / 20 °C
4: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C
5: 70 percent aq. HClO4 / 1 h / 20 °C
6: H2O / 0.08 h / Heating
7: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr
8: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C
9: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C
10: 73 percent / CH2Cl2 / 1 h / 20 °C
View Scheme
123664-84-6

N-(5-methoxy-2-phenoxyphenyl)methanesulfonamide

123663-49-0

Iguratimod

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C
2: 91 percent / acetone / 3 h
3: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C
4: 87 percent / dimethylformamide / 8 h / 15 °C
View Scheme
Multi-step reaction with 7 steps
1: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C
2: 70 percent aq. HClO4 / 1 h / 20 °C
3: H2O / 0.08 h / Heating
4: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr
5: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C
6: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C
7: 73 percent / CH2Cl2 / 1 h / 20 °C
View Scheme
123664-52-8

methyl 2-hydroxy-4-methylsulfonylamino-5-phenoxyphenyl ketone

123663-49-0

Iguratimod

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 70 percent aq. HClO4 / 1 h / 20 °C
2: H2O / 0.08 h / Heating
3: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr
4: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C
5: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C
6: 73 percent / CH2Cl2 / 1 h / 20 °C
View Scheme
123662-55-5

7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one

123663-49-0

Iguratimod

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr
2: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C
3: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C
4: 73 percent / CH2Cl2 / 1 h / 20 °C
View Scheme
123664-21-1

N-(4-oxo-6-phenoxy-2,3-dihydro-4H-7-chromenyl)methanesulfonamide

123663-49-0

Iguratimod

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C
2: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C
3: 73 percent / CH2Cl2 / 1 h / 20 °C
View Scheme
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  • Methanesulfonamide,N-[3-(formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]-

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Chemistry

Molecular Structure of Methanesulfonamide,N-[3-(formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]- (CAS NO.123663-49-0):

Molecular Formula: C17H14N2O6S
Molecular Weight: 374.3679
IUPAC Name: N-[7-(Methanesulfonamido)-4-oxo-6-phenoxychromen-3-yl]formamide
Synonyms of Methanesulfonamide,N-[3-(formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]- (CAS NO.123663-49-0): Iguratimod [INN] ; 3-Formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one ; Iguratimod ; N-(7-((Methylsulfonyl)amino)-4-oxo-6-phenoxy-4H-1-benzopyran-3-yl)formamide ; T 614 ; T-614 ; UNII-4IHY34Y2NV
CAS NO: 123663-49-0
Classification Code: API ; Pharmaceutical intermediate ; Pharmaceuticals 
Index of Refraction: 1.673
Molar Refractivity: 92.3 cm3
Molar Volume: 246 cm3
Surface Tension: 72.3 dyne/cm
Density: 1.52 g/cm3
Flash Point: 304.9 °C
Enthalpy of Vaporization: 86.84 kJ/mol
Boiling Point: 580.6 °C at 760 mmHg
Vapour Pressure of Methanesulfonamide,N-[3-(formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]- (CAS NO.123663-49-0): 1.8E-13 mmHg at 25°C