No renderable structure data available
C1=CC=C(C=C1)SCCNChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-phenylsulfanylethanamine |
|---|---|
| IUPAC Name | — |
| CAS Number | 2014-75-7 |
| Database ID | 37013 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-phenylsulfanylethanamine (CAS 2014-75-7) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 37013
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7304eb727e8c4b129ed129798753bc5bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0da61016e8c94b1aa8841cdfdbbd1381Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Isopropyl N-cyano-4-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (5 ml), and 2-phenylthioethylamine (0.49 g, 3.2 mmol) was added. The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residual concentrate was subjected to chromatography on a silica gel column (WAKO GEL C-200, 10 g) eluting with chloroform-methanol (50:1). The eluted fractions were concentrated under reduced pressure and crystallized from diethyl ether to give the title compound (0.49 g, 1.7 the reaction solution was concentrated under reduced pressure the residual concentrate eluting with chloroform-methanol (50:1) The eluted fractions were concentrated under reduced pressure crystallized from diethyl ether
Source ID: ord-bb1472f932f348a68f7dbe12a3bca3e5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Isopropyl N-cyano-4-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (5 ml), and 2-phenylthioethylamine (0.49 g, 3.2 mmol) was added. The mixture was stirred at room temperature for 2 hours After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residual concentrate was subjected to chromatography on a silica gel column (WAKO GEL C-200, 10 g) eluting with chloroform-methanol (50:1). The eluted fractions were concentrated under reduced pressure and crystallized from diethyl ether to give the title compound (0.49 g, 1.7 mmol, yield: 66%) as colorless crystals. the reaction solution was concentrated under reduced pressure the residual concentrate eluting with chloroform-methanol (50:1) The eluted fractions were concentrated under reduced pressure crystallized from diethyl ether
Source ID: ord-358eb9e37feb4c008aeed5bfc85eaaf2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Mix 2-aminoethanethiol hydrochloride (4.07 g, 35.6 mmol) in dioxane (75 mL) at 50° C. Add sodium hydride (60% in mineral oil, 2.84 g, 71.0 mmol) at room temperature under nitrogen. Stir the reaction for 5 minutes. Add 2-chloropyridine (3.5 mL, 37 mmol) to the mixture. Reflux the mixture for 24 hours, and then cool to room temperature. Add water (100 mL), and methylene chloride (300 mL) to this mixture. Extract the aqueous layer with methylene chloride (3×50 mL). Wash the combined organic phase with brine (200 mL), dry (magnesium sulfate), filter and concentrate to an orange oil. Perform flash chromatography on silica gel eluting with 50% (80:18:12 CHCl3/MeOH/concentrated NH4OH)/methylene chloride to afford the title compound as a yellow oil (1.67 g) m/e=155 (MH+). at room temperature the reaction for 5 minutes Reflux the mixture for 24 hours Extract the aqueous layer with methylene chloride (3×50 mL) Wash the combined organic phase with brine (200 mL) dry (magnesium sulfate) filter concentrate to an orange oil
Source ID: ord-4745645f1acc45048e76e058ecfb6dacConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: S-Methyl N-(5-bromo-3-pyridyl)-N'-cyanoisothiourea (650 mg) and 2-phenylthioethylamine (740 mg) in pyridine (0.5 ml) were heated to 50° C. for 5 hours. To the resulting clear solution was added ether (10 ml), and the desired pure compound was collected by filtration and washed with ether. the desired pure compound was collected by filtration washed with ether
Source ID: ord-262f92ccf08e488884e77e502fc46488Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: S-Methyl N-cyano-N'-3-pyridylisothiourea (1.92 g) was dissolved in pyridine (10 ml), and 2-phenylthioethylamine (3.06 g) was added. The mixture was kept at room temperature for 4 days, when it was evaporated in vacuo. The residue was triturated with ether (40 ml), and the resulting suspension was filtered and washed with ether. when it was evaporated in vacuo The residue was triturated with ether (40 ml) the resulting suspension was filtered washed with ether
Source ID: ord-404a26cd04d44b139f1a74d6ff7410edConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: S-Methyl N-cyano-N'-3-pyridylisothiourea (1.92 g) was dissolved in pyridine (10 ml), and 2-phenylthioethylamine (3.06 g) was added. The mixture was kept at room temperature for 4 days, when it was evaporated in vacuo. The residue was triturated with ether (40 ml), and the resulting suspension was filtered and washed with ether. when it was evaporated in vacuo The residue was triturated with ether (40 ml) the resulting suspension was filtered washed with ether
Source ID: ord-404a26cd04d44b139f1a74d6ff7410edConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The carboxylic acid from Step D, Example 1 (20.0 mg, 0.0625 mmol), 2-aminoethyl phenyl sulfide (9.6 mg, 0.0625 mmol), EDC hydrochloride (14.4 mg, 0.0751 mmol), HOBT (10.1 mg, 0.0751 mmol), and N,N-diisopropylethylamine (0.044 mL, 0.250 mmol) were stirred in dry, degassed DMF (1 mL) at 25° C. for 16 hours. The crude product was purified by preparative HPLC using a gradient of 5%-95% acetonitrile/0.1% TFA; 95%-5%/0.1% aqueous TFA over 15 min. The title compound was isolated after conversion to the HCl salt. MS (es) m+1=407. 1H-NMR (CD3OD): δ7.77 (s, 1H); 7.74 (d, 2H, J=8.3 Hz); 7.25-7.33 (m, 6H); 7.18 (t, 2H, J=7.2 Hz); 6.44 (bd, 1H, J=8.6 Hz); 4.77 (dd, 1H, J=11.8, 8.9 Hz); 3.91 (d, 1H, J=11.8 Hz), 3.40 (ddd, 2H, J=13.6, 6.8, 4.3 Hz); 3.00 (t, 2H, J=6.8 Hz). in dry degassed DMF (1 mL) at 25° C. for 16 hours The crude product was purified by preparative HPLC
Source ID: ord-815708992075445481b827b552fce1d2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The carboxylic acid from Step D, Example 1 (20.0 mg, 0.0625 mmol), 2-aminoethyl phenyl sulfide (9.6 mg, 0.0625 mmol), EDC hydrochloride (14.4 mg, 0.0751 mmol), HOBT (10.1 mg, 0.0751 mmol), and N,N-diisopropylethylamine (0.044 mL, 0.250 mmol) were stirred in dry, degassed DMF (1 mL) at 25° C. for 16 hours. The crude product was purified by preparative HPLC using a gradient of 5%-95% acetonitrile/0.1% TFA; 95%-5%/0.1% aqueous TFA over 15 min. The title compound was isolated after conversion to the HCl salt. MS (es) m+1=407. 1H-NMR (CD3OD): δ7.77 (s, 1H); 7.74 (d, 2H, J=8.3 Hz); 7.25-7.33 (m, 6H); 7.18 (t, 2H, J=7.2 Hz); 6.44 (bd, 1H, J=8.6 Hz); 4.77 (dd, 1H, J=11.8, 8.9 Hz); 3.91 (d, 1H, J=11.8 Hz), 3.40 (ddd, 2H, J=13.6, 6.8, 4.3 Hz); 3.00 (t, 2H, J=6.8 Hz). in dry degassed DMF (1 mL) at 25° C. for 16 hours The crude product was purified by preparative HPLC
Source ID: ord-815708992075445481b827b552fce1d2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Isopropyl N-cyano-4-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (5 ml), and 2-phenylthioethylamine (0.49 g, 3.2 mmol) was added. The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residual concentrate was subjected to chromatography on a silica gel column (WAKO GEL C-200, 10 g) eluting with chloroform-methanol (50:1). The eluted fractions were concentrated under reduced pressure and crystallized from diethyl ether to give the title compound (0.49 g, 1.7 the reaction solution was concentrated under reduced pressure the residual concentrate eluting with chloroform-methanol (50:1) The eluted fractions were concentrated under reduced pressure crystallized from diethyl ether
Source ID: ord-bb1472f932f348a68f7dbe12a3bca3e5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Isopropyl N-cyano-4-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (5 ml), and 2-phenylthioethylamine (0.49 g, 3.2 mmol) was added. The mixture was stirred at room temperature for 2 hours After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residual concentrate was subjected to chromatography on a silica gel column (WAKO GEL C-200, 10 g) eluting with chloroform-methanol (50:1). The eluted fractions were concentrated under reduced pressure and crystallized from diethyl ether to give the title compound (0.49 g, 1.7 mmol, yield: 66%) as colorless crystals. the reaction solution was concentrated under reduced pressure the residual concentrate eluting with chloroform-methanol (50:1) The eluted fractions were concentrated under reduced pressure crystallized from diethyl ether
Source ID: ord-358eb9e37feb4c008aeed5bfc85eaaf2PubChem References
These sources are listed in the compound's public database record.
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