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71675-87-1

Basic Information
CAS No.: 71675-87-1
Name: Benzoic acid,4-amino-5-(ethylsulfonyl)-2-methoxy-
Molecular Structure:
Molecular Structure of 71675-87-1 (Benzoic acid,4-amino-5-(ethylsulfonyl)-2-methoxy-)
Formula: C10H13NO5S
Molecular Weight: 259.28
Synonyms: 4-Amino-5-(ethylsulphonyl)-o-anisic acid;
EINECS: 275-833-8
Density: 1.39 g/cm3
Melting Point: 82-85 °C
Boiling Point: 529.6 °C at 760 mmHg
Flash Point: 274.1 °C
Solubility:
Appearance: Slightly pink solid
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 115.07000
LogP: 2.43120
Synthetic route
1119455-01-4

methyl 4-amino-5-(ethylthio)-2-methoxybenzoate

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

Conditions
ConditionsYield
Stage #1: methyl 4-amino-5-(ethylthio)-2-methoxybenzoate With dihydrogen peroxide; sodium tungstate In isopropyl alcohol at 40 - 45℃; Industry scale;
Stage #2: With water; sodium hydroxide In isopropyl alcohol at 60 - 65℃; Industry scale;
Stage #3: With hydrogenchloride In water; isopropyl alcohol pH=4 - 4.5; Industry scale;
82%
Multi-step reaction with 2 steps
1.1: sodium hydroxide; water / methanol / 65 °C / Industry scale
1.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale
2.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C
View Scheme

2-methoxy-4-amino-5-ethylthio benzoic acid

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide; sodium tungstate In methanol; water at 20 - 30℃; for 5h; Product distribution / selectivity;80%
27492-84-8

Methyl 4-amino-2-methoxybenzoate

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: bromine / methanol / 5 - 15 °C / Industry scale
2.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale
3.1: sodium hydroxide; water / methanol / 65 °C / Industry scale
3.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale
4.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: bromine / methanol / 5 - 15 °C / Industry scale
2.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale
3.1: dihydrogen peroxide / sodium tungstate / isopropyl alcohol / 40 - 45 °C / Industry scale
3.2: 60 - 65 °C / Industry scale
3.3: pH 4 - 4.5 / Industry scale
View Scheme
65-49-6

4-Aminosalicylic acid

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium hydroxide; tetrabutylammomium bromide / acetone / 1 h / 25 - 35 °C / Industry scale
2.1: bromine / methanol / 5 - 15 °C / Industry scale
3.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale
4.1: sodium hydroxide; water / methanol / 65 °C / Industry scale
4.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale
5.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium hydroxide; tetrabutylammomium bromide / acetone / 1 h / 25 - 35 °C / Industry scale
2.1: bromine / methanol / 5 - 15 °C / Industry scale
3.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale
4.1: dihydrogen peroxide / sodium tungstate / isopropyl alcohol / 40 - 45 °C / Industry scale
4.2: 60 - 65 °C / Industry scale
4.3: pH 4 - 4.5 / Industry scale
View Scheme
59168-56-8

methyl 4-amino-2-methoxy-5-thiocyanatobenzoate

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale
2.1: sodium hydroxide; water / methanol / 65 °C / Industry scale
2.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale
3.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale
2.1: dihydrogen peroxide / sodium tungstate / isopropyl alcohol / 40 - 45 °C / Industry scale
2.2: 60 - 65 °C / Industry scale
2.3: pH 4 - 4.5 / Industry scale
View Scheme
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

168828-90-8

(S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine

1390617-35-2

4-amino-5-(ethylsulfonyl)-N-(S)-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]-2-methoxybenzamide

Conditions
ConditionsYield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0 - 20℃; for 0.5h;
Stage #2: (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine In dichloromethane at 0 - 20℃; for 4h;
93%
26116-12-1

1-ethyl-2-pyrrolidinemethanamine

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

71675-85-9

amisulpride

Conditions
ConditionsYield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 10 - 20℃; for 1.5h;
Stage #2: 1-ethyl-2-pyrrolidinemethanamine With triethylamine In acetonitrile at 80℃; for 2h;
86.8%
With C36H24B4N2O3 In toluene for 14h; Molecular sieve; Reflux; chemoselective reaction;76%
With chloroformic acid ethyl ester; triethylamine In acetone at 0 - 30℃;70%
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

541-41-3

chloroformic acid ethyl ester

(-)-Amisulpride

Conditions
ConditionsYield
In acetone84%
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

C20H24N2O9S2

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25 - 40℃; for 12h; Reagent/catalyst; Solvent;72.52%

1-allyl 2-aminoethylpyrrolidine

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

541-41-3

chloroformic acid ethyl ester

71675-89-3

N-[1-allyl 2-pyrrolidylmethyl] 2-methoxy 4-amino 5-ethylsulphonyl benzamide

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In water; acetone67%
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

541-41-3

chloroformic acid ethyl ester

71820-57-0

(-)-(S)-2-Aminomethyl-1(cyclopropylmethyl)pyrrolidine

72135-20-7

LUR 2366

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water66.5%
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

148516-65-8

4-amino-5-(ethylsulfonyl)-2-hydroxybenzoic acid

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -50 - 20℃;65%
26116-12-1

1-ethyl-2-pyrrolidinemethanamine

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

541-41-3

chloroformic acid ethyl ester

71675-85-9

amisulpride

Conditions
ConditionsYield
With triethylamine In water; acetone61%
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

1-ethyl-2-aminomethylpyrrolidine hydrochloride

71675-85-9

amisulpride

Conditions
ConditionsYield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.5h;
Stage #2: 1-ethyl-2-aminomethylpyrrolidine hydrochloride With triethylamine In dichloromethane at 20℃;
29.7%

1-cyclohexylmethyl-pyrrolidin-3-R-ylamine

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

543-27-1

isobutyl chloroformate

A

55-21-0

benzamide

B

72135-95-6

N-(1-cyclohexylmethyl-3-pyrrolidinyl)-2-methoxy-4-amino-5-ethyl-sulphonyl-benzamide

Conditions
ConditionsYield
With triethylamine In water; ethyl acetate; acetone

1-cyclopropylmethyl-3-aminopyrrolidine

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

543-27-1

isobutyl chloroformate

72135-94-5

N-(1-cyclopropylmethyl-3-pyrrolidinyl)-2-methoxy-4-amino-5-ethyl-sulphonyl-benzamide

Conditions
ConditionsYield
With triethylamine In water; acetone; Diethyl carbonate
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

554-68-7

triethylamine hydrochloride

Conditions
ConditionsYield
With triethylamine In acetone
26171-06-2

1-methyl-2-aminomethyl-pyrrolidine

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

541-41-3

chloroformic acid ethyl ester

71675-88-2, 71675-93-9

N-(1-methyl-2-pyrrolidylmethyl)-2-methoxy-4-amino-5-ethylsulphonylbenzamid

Conditions
ConditionsYield
With triethylamine In water; acetone
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

22795-97-7

(R)-2-aminomethyl-1-ethylpyrrolidine

108-23-6

isopropyl chloroformate

(R)-(+)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions
ConditionsYield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid; isopropyl chloroformate With triethylamine In acetone at 5℃; for 0.5h;
Stage #2: (R)-2-aminomethyl-1-ethylpyrrolidine In acetone at 0 - 20℃; for 1.5h;
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

R-amisulpride maleic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / acetone / 0.5 h / 5 °C
1.2: 1.5 h / 0 - 20 °C
2.1: methanol / 5 h / 45 °C
View Scheme
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

(R)-(+)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide L-tartrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / acetone / 0.5 h / 5 °C
1.2: 1.5 h / 0 - 20 °C
2.1: methanol / 2 h / 40 - 45 °C
View Scheme
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

R-amisulpride hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / acetone / 0.5 h / 5 °C
1.2: 1.5 h / 0 - 20 °C
2.1: hydrogenchloride / water; methanol; diethyl ether / 2 h / 20 °C
View Scheme
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

(S)-N-(2,4-dimethoxybenzyl)-4-amino-N-((1-ethylpyrrolidin-2-yl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / acetone / 0.25 h / 0 - 10 °C / Inert atmosphere
1.2: 1.5 h / -5 - 5 °C
2.1: acetone / 4 h / 0 - 20 °C
View Scheme
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

(-)-Amisulpride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine / acetone / 0.25 h / 0 - 10 °C / Inert atmosphere
1.2: 1.5 h / -5 - 5 °C
2.1: acetone / 4 h / 0 - 20 °C
3.1: hydrogenchloride / methanol; water / 2 h / 20 °C
View Scheme
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

3282-30-2

pivaloyl chloride

4-amino-2-methoxy-5-ethylsulfonyl benzoate pivalic anhydride

Conditions
ConditionsYield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With triethylamine In acetone at 0 - 10℃; for 0.25h; Inert atmosphere;
Stage #2: pivaloyl chloride In acetone at -5 - 5℃; for 1.5h;
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

(-)-Amisulpride

Conditions
ConditionsYield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -10℃; for 1h; Inert atmosphere;
Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In acetone at -10 - 20℃; Temperature; Reagent/catalyst; Inert atmosphere;
49 g
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -8 - 0℃;
Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In acetone at 0 - 20℃; Temperature;
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -10℃; for 1h;
Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In tert-butyl methyl ether; ethyl acetate; acetone for 2h;
With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -8 - 20℃; Inert atmosphere;
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

(S)-(-)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide D-tartrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 4-methyl-morpholine; chloroformic acid ethyl ester / acetone / 1 h / -10 °C / Inert atmosphere
1.2: -10 - 20 °C / Inert atmosphere
2.1: methanol / 0.75 h / 22 °C
View Scheme
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

22795-97-7

(R)-2-aminomethyl-1-ethylpyrrolidine

(R)-(+)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions
ConditionsYield
With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -10 - 20℃; Temperature; Reagent/catalyst; Inert atmosphere;7 g
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -9℃; for 1h;
Stage #2: (R)-2-aminomethyl-1-ethylpyrrolidine In acetone for 16h; Temperature;
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -10℃; for 1h;
Stage #2: (R)-2-aminomethyl-1-ethylpyrrolidine In tert-butyl methyl ether; ethyl acetate; acetone for 2h;
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -9℃; for 1h;
Stage #2: (R)-2-aminomethyl-1-ethylpyrrolidine In acetone for 16h;
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    4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid

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    4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid

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Specification

The 4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid is an organic compound with the formula C10H13NO5S. The IUPAC name of this chemical is 4-amino-5-ethylsulfonyl-2-methoxybenzoic acid. With the CAS registry number 71675-87-1, it is also named as benzoic acid, 4-amino-5-(ethylsulfonyl)-2-methoxy-. The product's categories are Organic Acids; API Intermediates; Aromatics Compounds; Amines; Aromatics; Sulfur & Selenium Compounds. Besides, it is a slightly pink solid.

Physical properties about 4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid are: (1)ACD/LogP: 1.57; (2)ACD/LogD (pH 5.5): 0.15; (3)ACD/LogD (pH 7.4): -1.35; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 6.51; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 6; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 81.29 Å2; (12)Index of Refraction: 1.568; (13)Molar Refractivity: 61.08 cm3; (14)Molar Volume: 186.5 cm3; (15)Polarizability: 24.21×10-24cm3; (16)Surface Tension: 56 dyne/cm; (17)Density: 1.39 g/cm3; (18)Flash Point: 274.1 °C; (19)Enthalpy of Vaporization: 84.71 kJ/mol; (20)Boiling Point: 529.6 °C at 760 mmHg; (21)Vapour Pressure: 4.78E-12 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(c1c(cc(OC)c(C(=O)O)c1)N)CC
(2)InChI: InChI=1/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)
(3)InChIKey: OJVNCXHGGYYOPH-UHFFFAOYAY
(4)Std. 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)
(5)Std. InChIKey: OJVNCXHGGYYOPH-UHFFFAOYSA-N