Reaction #4103600
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0cdb38057745436cb46ae6ebc38b4998No renderable structure data available
C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)SClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | trityl thiohypochlorite |
|---|---|
| IUPAC Name | — |
| CAS Number | 24165-03-5 |
| Database ID | 342378 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
trityl thiohypochlorite (CAS 24165-03-5) 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 342378
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-0cdb38057745436cb46ae6ebc38b4998Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-hydroxyethyl)-3-amino-1-propanol (5.0 g, 41.9 mmol) is coevaporated several times with pyridine (20 mL) and then dissolved in pyridine (100 mL). The reaction flask is flushed with Argon and trimethylsilylchloride (2.47 g, 209.5 mmol) is added dropwise. The reaction mixture is stirred for 1 hour. Triphenyl methanesulfenyl chloride (14.32 g, 46.09 mmol) is dissolved in CH2Cl2 and added via dropping funnel to the cooled reaction mixture. The reaction mixture is warmed to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1). The H2O layer is separated and extracted with EtOAc (3×50 ml). The EtOAc extracts are pooled, dried (MgSO4) and filtered. The filtrate is concentrated in vacuo and the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound. is added dropwise added to the cooled reaction mixture stirred for 18 hours The reaction mixture is concentrated in vacuo the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1) The H2O layer is separated extracted with EtOAc (3×50 ml) dried (MgSO4) filtered The filtrate is concentrated in vacuo the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent concentrated in vacuo
Source ID: ord-990aa3d233b2451b872432b029293309Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-hydroxyethyl)-3-amino-1-propanol (5.0 g, 41.9 mmol) is coevaporated several times with pyridine (20 mL) and then dissolved in pyridine (100 mL). The reaction flask is flushed with Argon and trimethylsilylchloride (2.47 g, 209.5 mmol) is added dropwise. The reaction mixture is stirred for 1 hour. Triphenyl methanesulfenyl chloride (14.32 g, 46.09 mmol) is dissolved in CH2Cl2 and added via dropping funnel to the cooled reaction mixture. The reaction mixture is warmed to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1). The H2O layer is separated and extracted with EtOAc (3×50 ml). The EtOAc extracts are pooled, dried (MgSO4) and filtered. The filtrate is concentrated in vacuo and the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound. is added dropwise added to the cooled reaction mixture stirred for 18 hours The reaction mixture is concentrated in vacuo the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1) The H2O layer is separated extracted with EtOAc (3×50 ml) dried (MgSO4) filtered The filtrate is concentrated in vacuo the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent concentrated in vacuo
Source ID: ord-cf8487b5e33d45c7bec7cbeef436f326Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-hydroxyethyl)-3-amino-1-propanol (5.0 g, 41.9 mmol) is coevaporated several times with pyridine (20 mL) and then dissolved in pyridine (100 mL). The reaction flask is flushed with Argon and trimethylsilylchloride (2.47 g, 209.5 mmol) is added dropwise. The reaction mixture is stirred for 1 hour. Triphenyl methanesulfenyl chloride (14.32 g, 46.09 mmol) is dissolved in CH2Cl2 and added via dropping funnel to the cooled reaction mixture. The reaction mixture is warmed to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1). The H2O layer is separated and extracted with EtOAc (3×50 ml). The EtOAc extracts are pooled, dried (MgSO4) and filtered. The filtrate is concentrated in vacuo and the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound. is added dropwise added to the cooled reaction mixture stirred for 18 hours The reaction mixture is concentrated in vacuo the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1) The H2O layer is separated extracted with EtOAc (3×50 ml) dried (MgSO4) filtered The filtrate is concentrated in vacuo the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent concentrated in vacuo
Source ID: ord-990aa3d233b2451b872432b029293309Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-hydroxyethyl)-3-amino-1-propanol (5.0 g, 41.9 mmol) is coevaporated several times with pyridine (20 mL) and then dissolved in pyridine (100 mL). The reaction flask is flushed with Argon and trimethylsilylchloride (2.47 g, 209.5 mmol) is added dropwise. The reaction mixture is stirred for 1 hour. Triphenyl methanesulfenyl chloride (14.32 g, 46.09 mmol) is dissolved in CH2Cl2 and added via dropping funnel to the cooled reaction mixture. The reaction mixture is warmed to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1). The H2O layer is separated and extracted with EtOAc (3×50 ml). The EtOAc extracts are pooled, dried (MgSO4) and filtered. The filtrate is concentrated in vacuo and the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound. is added dropwise added to the cooled reaction mixture stirred for 18 hours The reaction mixture is concentrated in vacuo the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1) The H2O layer is separated extracted with EtOAc (3×50 ml) dried (MgSO4) filtered The filtrate is concentrated in vacuo the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent concentrated in vacuo
Source ID: ord-990aa3d233b2451b872432b029293309Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0cdb38057745436cb46ae6ebc38b4998Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-hydroxyethyl)-3-amino-1-propanol (5.0 g, 41.9 mmol) is coevaporated several times with pyridine (20 mL) and then dissolved in pyridine (100 mL). The reaction flask is flushed with Argon and trimethylsilylchloride (2.47 g, 209.5 mmol) is added dropwise. The reaction mixture is stirred for 1 hour. Triphenyl methanesulfenyl chloride (14.32 g, 46.09 mmol) is dissolved in CH2Cl2 and added via dropping funnel to the cooled reaction mixture. The reaction mixture is warmed to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1). The H2O layer is separated and extracted with EtOAc (3×50 ml). The EtOAc extracts are pooled, dried (MgSO4) and filtered. The filtrate is concentrated in vacuo and the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound. is added dropwise added to the cooled reaction mixture stirred for 18 hours The reaction mixture is concentrated in vacuo the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1) The H2O layer is separated extracted with EtOAc (3×50 ml) dried (MgSO4) filtered The filtrate is concentrated in vacuo the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent concentrated in vacuo
Source ID: ord-ea0705d3d39e439a983215f7d015a9b4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-hydroxyethyl)-3-amino-1-propanol (5.0 g, 41.9 mmol) is coevaporated several times with pyridine (20 mL) and then dissolved in pyridine (100 mL). The reaction flask is flushed with Argon and trimethylsilylchloride (2.47 g, 209.5 mmol) is added dropwise. The reaction mixture is stirred for 1 hour. Triphenyl methanesulfenyl chloride (14.32 g, 46.09 mmol) is dissolved in CH2Cl2 and added via dropping funnel to the cooled reaction mixture. The reaction mixture is warmed to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1). The H2O layer is separated and extracted with EtOAc (3×50 ml). The EtOAc extracts are pooled, dried (MgSO4) and filtered. The filtrate is concentrated in vacuo and the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound. is added dropwise added to the cooled reaction mixture stirred for 18 hours The reaction mixture is concentrated in vacuo the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1) The H2O layer is separated extracted with EtOAc (3×50 ml) dried (MgSO4) filtered The filtrate is concentrated in vacuo the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent concentrated in vacuo
Source ID: ord-ea0705d3d39e439a983215f7d015a9b4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-hydroxyethyl)-3-amino-1-propanol (5.0 g, 41.9 mmol) is coevaporated several times with pyridine (20 mL) and then dissolved in pyridine (100 mL). The reaction flask is flushed with Argon and trimethylsilylchloride (2.47 g, 209.5 mmol) is added dropwise. The reaction mixture is stirred for 1 hour. Triphenyl methanesulfenyl chloride (14.32 g, 46.09 mmol) is dissolved in CH2Cl2 and added via dropping funnel to the cooled reaction mixture. The reaction mixture is warmed to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1). The H2O layer is separated and extracted with EtOAc (3×50 ml). The EtOAc extracts are pooled, dried (MgSO4) and filtered. The filtrate is concentrated in vacuo and the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound. is added dropwise added to the cooled reaction mixture stirred for 18 hours The reaction mixture is concentrated in vacuo the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1) The H2O layer is separated extracted with EtOAc (3×50 ml) dried (MgSO4) filtered The filtrate is concentrated in vacuo the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent concentrated in vacuo
Source ID: ord-ea0705d3d39e439a983215f7d015a9b4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-hydroxyethyl)-3-amino-1-propanol (5.0 g, 41.9 mmol) is coevaporated several times with pyridine (20 mL) and then dissolved in pyridine (100 mL). The reaction flask is flushed with Argon and trimethylsilylchloride (2.47 g, 209.5 mmol) is added dropwise. The reaction mixture is stirred for 1 hour. Triphenyl methanesulfenyl chloride (14.32 g, 46.09 mmol) is dissolved in CH2Cl2 and added via dropping funnel to the cooled reaction mixture. The reaction mixture is warmed to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1). The H2O layer is separated and extracted with EtOAc (3×50 ml). The EtOAc extracts are pooled, dried (MgSO4) and filtered. The filtrate is concentrated in vacuo and the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound. is added dropwise added to the cooled reaction mixture stirred for 18 hours The reaction mixture is concentrated in vacuo the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1) The H2O layer is separated extracted with EtOAc (3×50 ml) dried (MgSO4) filtered The filtrate is concentrated in vacuo the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent concentrated in vacuo
Source ID: ord-b5bb93f8bf0446fe8b676944fe36c149Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-Hydroxyethyl)-3-amino-1-propanol (5.0 g, 41.9 mmol) is coevaporated several times with pyridine (20 mL) and then dissolved in pyridine (100 mL). The reaction flask is flushed with Argon and trimethylsilylchloride (2.47 g, 209.5 mmol) is added dropwise. The reaction mixture is stirred for 1 hour. Triphenyl methanesulfenyl chloride (14.32 g, 46.09 mmol) is dissolved in CH2Cl2and added via dropping funnel to the cooled reaction mixture. The reaction mixture is warmed to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1). The H2O layer is separated and extracted with EtOAc (3×50 ml). The EtOAc extracts are pooled, dried (MgSO4) and filtered. The filtrate is concentrated in vacuo and the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound. is added dropwise added to the cooled reaction mixture stirred for 18 hours The reaction mixture is concentrated in vacuo the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1) The H2O layer is separated extracted with EtOAc (3×50 ml) dried (MgSO4) filtered The filtrate is concentrated in vacuo the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent concentrated in vacuo
Source ID: ord-6e10cbf56d4e4709b03da78a5175a331Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-hydroxyethyl)-3-amino-1-propanol (5.0 g, 41.9 mmol) is coevaporated several times with pyridine (20 mL) and then dissolved in pyridine (100 mL). The reaction flask is flushed with Argon and trimethylsilylchloride (2.47 g, 209.5 mmol) is added dropwise. The reaction mixture is stirred for 1 hour. Triphenyl methanesulfenyl chloride (14.32 g, 46.09 mmol) is dissolved in CH2Cl2 and added via dropping funnel to the cooled reaction mixture. The reaction mixture is warmed to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1). The H2O layer is separated and extracted with EtOAc (3×50 ml). The EtOAc extracts are pooled, dried (MgSO4) and filtered. The filtrate is concentrated in vacuo and the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound. is added dropwise added to the cooled reaction mixture stirred for 18 hours The reaction mixture is concentrated in vacuo the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1) The H2O layer is separated extracted with EtOAc (3×50 ml) dried (MgSO4) filtered The filtrate is concentrated in vacuo the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent concentrated in vacuo
Source ID: ord-b8c4901269bb44d09895c477633b6605PubChem References
These sources are listed in the compound's public database record.
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