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1010396-29-8

Basic Information
CAS No.: 1010396-29-8
Name: S-23
Article Data: 3
Molecular Structure:
Molecular Structure of 1010396-29-8 (S-23)
Formula: C18H13ClF4N2O3
Molecular Weight: 416.759
Synonyms: S-23;(S)-3-(4-Chloro-3-fluorophenoxy)-N-(4-cyano-3-trifluoromethylphenyl)-2-hydroxy-2-methylpropionamide;(2S)-3-(4-Chloro-3-fluorophenoxy)-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide;S 23 (contraceptive)
EINECS: -0
Density: 1.48±0.1 g/cm3(Predicted)
Melting Point: 119-121 °C
Boiling Point: 577.1±50.0 °C(Predicted)
Hazard Symbols: 19161994
Risk Codes: 19161994
PSA: 82.35000
LogP: 4.21108
Synthetic route
348-60-7

4-chloro-3-fluorophenol

206193-17-1

(2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide

1010396-29-8

(S)-3-(4-chloro-3-fluorophenoxy)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide

Conditions
ConditionsYield
Stage #1: (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide With potassium carbonate for 2h; Reflux;
Stage #2: 4-chloro-3-fluorophenol With potassium carbonate In isopropyl alcohol for 3h; Reflux;
70.5%
With potassium carbonate In isopropyl alcohol for 3h; Reflux;70.5%
512776-95-3

(2S)-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide

348-60-7

4-chloro-3-fluorophenol

1010396-29-8

(S)-3-(4-chloro-3-fluorophenoxy)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide

Conditions
ConditionsYield
With potassium carbonate In butanone Reflux;
654-70-6

4-amino-2-trifluoromethylbenzonitrile

1010396-29-8

(S)-3-(4-chloro-3-fluorophenoxy)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: thionyl chloride / tetrahydrofuran / 3 h / 4 °C / Inert atmosphere
1.2: 20 °C
2.1: potassium carbonate / isopropyl alcohol / 3 h / Reflux
View Scheme
1010396-29-8

(S)-3-(4-chloro-3-fluorophenoxy)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide

79-44-7

N,N-Dimethylcarbamoyl chloride

(S)-1-(4-cyano-3-(trifluoromethyl)anilino)-3-(4-chloro-3-fluorophenoxyl)-2-methyl-1-oxopropyl dimethylcarbamate

Conditions
ConditionsYield
Stage #1: (S)-3-(4-chloro-3-fluorophenoxy)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃;
Stage #2: N,N-Dimethylcarbamoyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃;
155 g
1010396-29-8

(S)-3-(4-chloro-3-fluorophenoxy)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide

124-63-0

methanesulfonyl chloride

(S)-1-(4-cyano-3-(trifluoromethyl)anilino)-3-(4-chloro-3-fluorophenoxyl)-2-methyl-1-oxopropyl methanesulfonate

Conditions
ConditionsYield
Stage #1: (S)-3-(4-chloro-3-fluorophenoxy)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide With sodium hydride In tetrahydrofuran; mineral oil at 0℃;
Stage #2: methanesulfonyl chloride In tetrahydrofuran; mineral oil at 20℃;
2051-49-2

n-hexanoic anhydride

1010396-29-8

(S)-3-(4-chloro-3-fluorophenoxy)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide

(S)-1-(4-cyano-3-(trifluoromethyl)anilino)-3-(4-chloro-3-fluorophenoxyl)-2-methyl-1-oxopropyl pentanoate

Conditions
ConditionsYield
In pyridine Reflux;70 g
1010396-29-8

(S)-3-(4-chloro-3-fluorophenoxy)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide

108-24-7

acetic anhydride

(S)-1-(4-cyano-3-(trifluoromethyl)anilino)-3-(4-chloro-3-fluorophenoxyl)-2-methyl-1-oxopropyl acetate

Conditions
ConditionsYield
In pyridine Reflux;0.4 g
16837-38-0

nicotinic anhydride

1010396-29-8

(S)-3-(4-chloro-3-fluorophenoxy)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide

(S)-1-(4-cyano-3-(trifluoromethyl)anilino)-3-(4-chloro-3-fluorophenoxyl)-2-methyl-1-oxopropyl pyridine-3-carboxylate

Conditions
ConditionsYield
In pyridine for 10h; Reflux;100 g
1010396-29-8

(S)-3-(4-chloro-3-fluorophenoxy)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide

93-97-0

benzoic acid anhydride

(S)-1-(4-cyano-3-(trifluoromethyl)anilino)-3-(4-chloro-3-fluorophenoxyl)-2-methyl-1-oxopropyl benzoate

Conditions
ConditionsYield
In pyridine117 g
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    S-23 Chemical Properties Melting point 119-121 °C Boiling point 577.1±50.0 °C(Predicted) density 1.48±0.1 g/cm3(Predicted) form neat pka 12.04±0.29(Predicted) optical activity [α]/D 20±3

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