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Basic Information
| CAS No.: | 253168-94-4 |
|---|---|
| Name: | 3-Ethoxy-4-Methoxy-alpha-[(Methylsulfonyl)Methyl]-benzeneMethanaMine |
| Article Data: | 22 |
| Molecular Structure: | |
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| Formula: | C12H19 NO4S |
| Molecular Weight: | 273.353 |
| Synonyms: | 2-(3-ethoxy-4-methoxyphenyl-1-methylsulphonyl)-eth-2-ylamine; 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine; 1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine; 1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine; 1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine; 2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulphonyl)-eth-2-ylamine; Apremilast Intermediate I; 3-Ethoxy-4-methoxy-alpha-[(methylsulfonyl)methyl]-benzenemethanamine; Benzenemethanamine, 3-ethoxy-4-methoxy-a-[(methylsulfonyl)methyl]-; 2-(3-ethoxy-4-methoxyphenyl)-1-(methanesulfonyl)-eth-2-ylamine; 1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine; ApreMilast interMediate; 查看更多英文别名 收起 |
| EINECS: | 807-312-3 |
| Density: | 1.195±0.06 g/cm3(Predicted) |
| Melting Point: | 120 °C |
| Boiling Point: | 469.6±45.0 °C(Predicted) |
| PSA: | 87.00000 |
| LogP: | 2.91940 |
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Synthetic route
- 253168-94-4
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
Conditions
| Conditions | Yield |
|---|---|
| With isopropanol hydrochloride In acetonitrile at 25 - 30℃; for 12h; | 95% |
| With hydrogenchloride In water; toluene at 65 - 70℃; for 1h; | 145 g |
- 67-71-0
dimethylsulfone
- 1131-52-8
3-ethoxy-4-methoxybenzaldehyde
- 253168-94-4
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: dimethylsulfone With n-butyllithium In tetrahydrofuran; hexane at -20 - 0℃; for 1h; Stage #2: 3-ethoxy-4-methoxybenzaldehyde With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -40 - -30℃; for 1h; Stage #3: With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -30 - 0℃; Temperature; | 91.5% |
| Stage #1: 3-ethoxy-4-methoxybenzaldehyde With lithium hexamethyldisilazane at -78℃; Stage #2: dimethylsulfone With n-butyllithium; boron trifluoride diethyl etherate at -78℃; | 41% |
- 253168-94-4
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
Conditions
| Conditions | Yield |
|---|---|
| With acetic acid; zinc | 91% |
- 1450657-31-4
1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethen-1-amine
- 253168-94-4
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
Conditions
| Conditions | Yield |
|---|---|
| With sodium cyanoborohydride; citric acid In methanol at 5℃; for 1h; Reagent/catalyst; Temperature; Concentration; Solvent; | 88% |
- 1450657-28-9
1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethan-1-one
- 253168-94-4
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
Conditions
| Conditions | Yield |
|---|---|
| With palladium on activated charcoal; ammonium formate In methanol; water for 15h; Reflux; | 87.8% |
| Stage #1: 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethan-1-one With ammonium acetate In methanol; water for 1h; Reflux; Stage #2: With sodium tris(acetoxy)borohydride In methanol; water at 0 - 10℃; for 7h; | 75.3% |
| With ammonium formate In methanol; water for 20h; Reflux; | 42.4% |
- 253168-94-4
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
Conditions
| Conditions | Yield |
|---|---|
| With triphenylphosphine In tetrahydrofuran; water at 60℃; for 6h; Sealed tube; Inert atmosphere; | 87% |
- 52849-52-2
1-Bromo-3-ethoxy-4-methoxybenzene
- 2274-42-2
methanesulfonyl-acetonitrile
- 253168-94-4
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: 1-Bromo-3-ethoxy-4-methoxybenzene With iodine; magnesium In tetrahydrofuran at 45 - 60℃; for 3.83333h; Stage #2: methanesulfonyl-acetonitrile With hydroxylamine hydrochloride In tetrahydrofuran at -5 - 0℃; for 3.66667h; Stage #3: With hydrogen In tetrahydrofuran at 20 - 25℃; under 760.051 - 1520.1 Torr; for 3h; Reagent/catalyst; Solvent; Autoclave; | 86.5% |
- 2516-97-4
2-(methylsulfonyl)acetic acid
- 1131-52-8
3-ethoxy-4-methoxybenzaldehyde
- 253168-94-4
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
Conditions
| Conditions | Yield |
|---|---|
| With thionyl chloride; ammonium acetate In ethanol for 16h; Reflux; | 78% |
- 67-71-0
dimethylsulfone
- 60758-86-3
3-ethoxy-4-methoxybenzenecarbonitrile
- 253168-94-4
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: dimethylsulfone With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; Stage #2: 3-ethoxy-4-methoxybenzenecarbonitrile In tetrahydrofuran; hexane at 0 - 20℃; Product distribution / selectivity; Inert atmosphere; | 76.1% |
| Stage #1: dimethylsulfone With potassium hexamethylsilazane In tetrahydrofuran at 0 - 10℃; for 1h; Large scale; Stage #2: 3-ethoxy-4-methoxybenzenecarbonitrile In tetrahydrofuran for 0.5h; Large scale; Stage #3: With sodium tetrahydroborate; acetic acid In tetrahydrofuran at 0 - 62℃; Temperature; Large scale; | 65% |
| Stage #1: dimethylsulfone With potassium tert-butylate In dimethyl sulfoxide at 30℃; for 3h; Stage #2: 3-ethoxy-4-methoxybenzenecarbonitrile In tetrahydrofuran; dimethyl sulfoxide for 3.5h; Stage #3: With sodium tetrahydroborate In tetrahydrofuran; dimethyl sulfoxide at 30℃; for 1h; | 50% |
| Stage #1: dimethylsulfone With n-butyllithium In tetrahydrofuran at 0 - 5℃; for 1.5h; Stage #2: 3-ethoxy-4-methoxybenzenecarbonitrile In tetrahydrofuran at 0 - 30℃; for 1.5h; Further stages; |
- 253168-94-4
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: (E)-2-ethoxy-1-methoxy-4-(2-(methylsulfonyl)vinyl)benzene With boric acid In water at 50 - 60℃; for 0.166667h; Stage #2: With ammonium hydroxide In water at 80℃; for 72h; Reagent/catalyst; Temperature; | 75% |
| Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; triethylamine / ethanol / 24 h / 80 °C 2: zinc; acetic acid View Scheme |
