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221615-72-1

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Basic Information
CAS No.: 221615-72-1
Name: 1-(6-Methylpyridin-3-yl)-2-(4-(Methylthio)phenyl)ethanone
Article Data: 11
Molecular Structure:
Molecular Structure of 221615-72-1 (1-(6-Methylpyridin-3-yl)-2-(4-(Methylthio)phenyl)ethanone)
Formula: C15H15NOS
Molecular Weight: 257.356
Synonyms: Etoricoxib Intermediate 1;1-(6-Methylpyridin-3-yl)-2-(4-(Methylthio)phenyl)ethanone;1-(6-Methyl-3-pyridinyl)-2-[4-(Methylthio)phenyl]-ethanone;1-(6-Methylpyridin-3-yl)-2-(4-(methylthio)phenyl)ethan-1-one;1-(6-Methyl-3-pyridinyl)-2-[4-(methylsulfanyl)phenyl]ethanone;1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone;Ethanone, 1-?(6-?methyl-?3-?pyridinyl)?-?2-?[4-?(methylthio)?phenyl]?-;Etoricoxib impurity 14/1-(6-Methylpyridin-3-yl)-2-[4-(methylthio)phenyl]ethanone
EINECS: 807-172-3
Density: 1.17±0.1 g/cm3(Predicted)
Melting Point: 111-113℃
Boiling Point: 426.7±40.0 °C(Predicted)
PSA: 55.26000
LogP: 3.53730
Related products
Synthetic route
5470-70-2

Methyl 6-methylnicotinate

lithium 4-(methylthio)phenylacetate

221615-72-1

1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1h; Reagent/catalyst; Temperature;87.7%
221615-71-0

N-methoxy-N-methyl-6-methylnicotinamide

4-(methylthio)benzylmagnesium chloride

221615-72-1

1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone

Conditions
ConditionsYield
In tetrahydrofuran; toluene at -10℃; for 1h;80%
5470-70-2

Methyl 6-methylnicotinate

sodium 4-(methylthio)phenylacetate

221615-72-1

1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1h;78.5%
874-87-3

1-(chloromethyl)-4-methylthiobenzene

221615-71-0

N-methoxy-N-methyl-6-methylnicotinamide

221615-72-1

1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone

Conditions
ConditionsYield
Stage #1: 1-(chloromethyl)-4-methylthiobenzene With magnesium In tetrahydrofuran; toluene for 3 - 4h;
Stage #2: N-methoxy-N-methyl-6-methylnicotinamide In toluene at -20℃; for 1.5h;		76%
With magnesium; ethylene dibromide In tetrahydrofuran; toluene at 36℃;62%
5470-70-2

Methyl 6-methylnicotinate

16188-55-9

2-(4-(methylthio)phenyl)acetic acid

221615-72-1

1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1h;72%
Stage #1: 2-(4-(methylthio)phenyl)acetic acid With tert-butylmagnesium chloride In tetrahydrofuran at 60℃; for 1h; Flow reactor;
Stage #2: Methyl 6-methylnicotinate In tetrahydrofuran at 60℃; for 1h; Flow reactor;
Stage #3: With hydrogenchloride In water; toluene Temperature; Flow reactor;

isoxazolidine-2-yl-(6-methylpyridin-3-yl)methanone

4-(methylthio)benzylmagnesium chloride

221615-72-1

1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone

Conditions
ConditionsYield
In tetrahydrofuran; toluene at -20 - -10℃; for 1h; Temperature; Inert atmosphere;60%
5470-70-2

Methyl 6-methylnicotinate

221615-72-1

1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: i-PrMgCl / toluene; tetrahydrofuran / 0.5 h / -10 °C
2: 80 percent / tetrahydrofuran; toluene / 1 h / -10 °C
View Scheme
Multi-step reaction with 2 steps
1.1: toluene / 0.67 h / Reflux
1.2: Reflux
2.1: hydrogenchloride; water; acetic acid / 40 °C / Reflux
2.2: 0.17 h / 0 - 5 °C / pH 7 - 7.2
View Scheme
Multi-step reaction with 2 steps
1: sodium methylate / toluene / 0.67 h / 25 - 30 °C / pH 5.2-6.2 / Reflux
2: hydrogenchloride / toluene; water; acetic acid / 20 °C / pH 6.9-7.1
View Scheme
Multi-step reaction with 2 steps
1: isopropylmagnesium chloride / toluene; tetrahydrofuran / 0.5 h / -20 - -10 °C / Inert atmosphere
2: toluene; tetrahydrofuran / 1 h / -20 - -10 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: isopropylmagnesium chloride / toluene; tetrahydrofuran / 0.5 h / -20 - -10 °C / Inert atmosphere
2: diethyl ether / -10 - 0 °C
View Scheme
38746-92-8

2-[4-(methylsulfanyl)phenyl]acetonitrile

221615-72-1

1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene / 0.67 h / Reflux
1.2: Reflux
2.1: hydrogenchloride; water; acetic acid / 40 °C / Reflux
2.2: 0.17 h / 0 - 5 °C / pH 7 - 7.2
View Scheme
Multi-step reaction with 2 steps
1: sodium methylate / toluene / 0.67 h / 25 - 30 °C / pH 5.2-6.2 / Reflux
2: hydrogenchloride / toluene; water; acetic acid / 20 °C / pH 6.9-7.1
View Scheme
321913-54-6

1-(6-methyl-3-pyridinyl)-2-cyano-2-[(4-methylthio)phenyl]ethanone

221615-72-1

1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone

Conditions
ConditionsYield
Stage #1: 1-(6-methyl-3-pyridinyl)-2-cyano-2-[(4-methylthio)phenyl]ethanone With hydrogenchloride; water; acetic acid at 40℃; Reflux;
Stage #2: With ammonia In water at 0 - 5℃; for 0.166667h; pH=7 - 7.2; Product distribution / selectivity;
With hydrogenchloride In water; acetic acid; toluene at 20℃; pH=6.9-7.1; Concentration; Reagent/catalyst; Solvent; Time; Temperature;5.2 g
5470-70-2

Methyl 6-methylnicotinate

38746-92-8

2-[4-(methylsulfanyl)phenyl]acetonitrile

221615-72-1

1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone

Conditions
ConditionsYield
Stage #1: Methyl 6-methylnicotinate; 2-[4-(methylsulfanyl)phenyl]acetonitrile With hydrogenchloride; sodium methylate In water; toluene at 25 - 30℃; pH=5.2-6.2; Reflux;
Stage #2: With hydrogenchloride In water; acetic acid; toluene at 40 - 50℃; Reflux;
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