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| CAS No.: | 1010396-29-8 |
|---|---|
| Name: | S-23 |
| Molecular Structure: | |
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| 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 |

4-chloro-3-fluorophenol


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


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

| Conditions | Yield |
|---|---|
| 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% |

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


4-chloro-3-fluorophenol


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

| Conditions | Yield |
|---|---|
| With potassium carbonate In butanone Reflux; |

4-amino-2-trifluoromethylbenzonitrile


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

| Conditions | Yield |
|---|---|
| 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 |

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


N,N-Dimethylcarbamoyl chloride

| Conditions | Yield |
|---|---|
| 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 |

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


methanesulfonyl chloride

| Conditions | Yield |
|---|---|
| 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℃; |

n-hexanoic anhydride


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

| Conditions | Yield |
|---|---|
| In pyridine Reflux; | 70 g |

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


acetic anhydride

| Conditions | Yield |
|---|---|
| In pyridine Reflux; | 0.4 g |

nicotinic anhydride


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

| Conditions | Yield |
|---|---|
| In pyridine for 10h; Reflux; | 100 g |

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


benzoic acid anhydride

| Conditions | Yield |
|---|---|
| In pyridine | 117 g |