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[ CAS No. 14316-14-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 14316-14-4
Chemical Structure| 14316-14-4
Chemical Structure| 14316-14-4
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Product Details of [ 14316-14-4 ]

CAS No. :14316-14-4 MDL No. :MFCD00464177
Formula : C9H13NO3S Boiling Point : -
Linear Structure Formula :- InChI Key :SIIWTWXTZDDNTI-UHFFFAOYSA-N
M.W : 215.27 Pubchem ID :1895595
Synonyms :

Calculated chemistry of [ 14316-14-4 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 53.27
TPSA : 74.78 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.41
Log Po/w (XLOGP3) : 0.57
Log Po/w (WLOGP) : 1.35
Log Po/w (MLOGP) : 0.43
Log Po/w (SILICOS-IT) : 0.55
Consensus Log Po/w : 0.86

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.59
Solubility : 5.57 mg/ml ; 0.0259 mol/l
Class : Very soluble
Log S (Ali) : -1.71
Solubility : 4.17 mg/ml ; 0.0194 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.214 mg/ml ; 0.000993 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.16

Safety of [ 14316-14-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14316-14-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 14316-14-4 ]

[ 14316-14-4 ] Synthesis Path-Downstream   1~87

  • 1
  • [ 141-43-5 ]
  • [ 98-59-9 ]
  • [ 14316-14-4 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;
99% With triethylamine In dichloromethane at 0 - 20℃; for 24h;
96% With pyridine at 5 - 20℃;
94% With triethylamine In dichloromethane at 0 - 20℃; for 2h;
91% With zinc oxide-nanoparticle at 50℃; Neat (no solvent); chemoselective reaction;
90% With tetrabutylammomium bromide; sodium hydroxide In benzene at 0 - 20℃; for 8h;
90% With tetrabutylammomium bromide; sodium hydroxide In benzene at 0 - 20℃; for 8h;
89% With sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 3h; stereoselective reaction;
89% With triethylamine In dichloromethane at 0 - 20℃;
85% With triethylamine In dichloromethane at 20℃;
83% With triethylamine In dichloromethane at 0 - 20℃; for 18h;
81% With triethylamine In dichloromethane at 0 - 25℃; for 0.333333h;
70% In toluene Heating;
70% With triethylamine In dichloromethane at 0 - 20℃;
70% With triethylamine In dichloromethane at 20℃; for 18h; Schlenk technique; Cooling with ice;
68% With triethylamine In dichloromethane at 0℃; for 8h;
68% With triethylamine In dichloromethane at 20℃; for 17h; Sealed tube; Inert atmosphere;
61% With triethylamine In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere; Cooling with ice;
43% With dmap; triethylamine In dichloromethane at 0 - 20℃; General procedure for the preparation of N-protected aminoalcohols General procedure: To a solution of aminoalcohol (10 mmol), DMAP (1 mmol) and triethylamine (20 mmol) in CH2Cl2(2.0 M) at 0 °C, a solution of the suitable sulfonyl chloride was added dropwise (10.5 mmol) inCH2Cl2 (50 mL) and the resulting mixture was stirred at room temperature overnight. The mixturewas washed with water (3 x 50 mL) and brine (1 x 50 mL), then dried over Na2SO4, andconcentrated at reduced pressure. The crude product was purified by silica gel columnchromatography to afford the corresponding protected aminoalcohol.
With pyridine
With sodium hydroxide
With sodium hydroxide In benzene
In N,N-dimethyl-formamide
With hydrogenchloride In dichloromethane; water a I. a) 100 g of p-toluenesulfonyl chloride are slowly added over 1.5 hour to 80 ml of ethanolamine while cooling with ice. The reaction mixture is then heated to 120° C. and is then held at this temperature for 3 hours. After cooling to 70° C., a mixture of 60 ml of concentration HCl and 300 ml of water is added. After stirring for 10 min, 300 ml of methylene chloride are added, and the organic phase is separated and dried with MgSO4. After stripping off the solvent on the rotary evaporator, 111.6 g of a slightly yellowish solid [N-(2-hydroxyethyl)-p-toluenesulfonamide] are obtained. The product can be used in the next step without further purification.
With sodium hydroxide; tetrabutylammomium bromide In water; benzene
With triethylamine In tetrahydrofuran; water at 0 - 20℃;
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
With triethylamine In dichloromethane at 20℃; for 16h;
With triethylamine In dichloromethane at 20℃;
With triethylamine In chloroform at 20℃; for 16h;
With triethylamine In dichloromethane
With triethylamine In dichloromethane at 20℃;
With silica gel for 0.5h; Inert atmosphere;
With triethylamine In dichloromethane at 20℃;
With triethylamine In dichloromethane at 20℃;
With silica gel Inert atmosphere;
In ethyl acetate at 20℃; for 2h; Typical procedure for the synthesis of starting materials General procedure: Tosylation: To a solution of p-toluenesulfonyl chloride (5 mmol, 1.0 equiv) in EtOAc (10 mL) was added proper alkanolamine (10 mmol, 2.0 equiv). The reaction mixture was stirred for 2 hours at room temperature. After completion of the reaction, the mixture was filtered through silica and washed with EtOAc. The residue was concentrated to give products, which were used to next step without further purification.
2 g With triethylamine In dichloromethane at 20℃; Inert atmosphere;
With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere; Schlenk technique;
With triethylamine In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;
With dmap; triethylamine In dichloromethane at 0 - 20℃;
With triethylamine In dichloromethane at 20℃; for 3h; Inert atmosphere;

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  • 4
  • [ 14316-14-4 ]
  • [ 111-44-4 ]
  • [ 50977-94-1 ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate In N,N-dimethyl-formamide
65% With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 24h;
(i) KOtBu, (ii) /BRN= 605317/; Multistep reaction;
  • 5
  • [ 29981-92-8 ]
  • [ 141-43-5 ]
  • [ 14316-14-4 ]
  • [ 35487-17-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; tetramethlyammonium chloride In ethanol at 25℃; μ=0.16 M;
  • 6
  • [ 141-43-5 ]
  • [ 2232-08-8 ]
  • [ 288-32-4 ]
  • [ 14316-14-4 ]
  • 7
  • [ 14316-14-4 ]
  • [ 18162-48-6 ]
  • [ 202974-92-3 ]
YieldReaction ConditionsOperation in experiment
93% With 1H-imidazole In dichloromethane at 20℃; for 22h; Inert atmosphere;
90% With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 15h;
84% With 1H-imidazole In dichloromethane at 25℃; for 22h;
72% With 1H-imidazole In N,N-dimethyl-formamide at 20℃; General procedure for the preparation of O-(tert-butyldimethylsilyl)-N-protectedaminoalcohol General procedure: A solution of N-protected aminoalcohol (10 mmol), tert-butyldimethylsilyl chloride (20 mmol) andimidazole (20 mmol) in DMF (0.2 M) was stirred at room temperature overnight. The reaction wastaken with brine (40 mL), extracted with Et2O (3 x 40 mL), dried over Na2SO4 and concentrated atreduced pressure. The crude product was purified by silica gel column chromatography to affordthe corresponding O-(tert-butyldimethylsilyl)-N-protected aminoalcohol.3
With 1H-imidazole In N,N-dimethyl-formamide Yield given;
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h;
With 1H-imidazole In dichloromethane at 0℃; for 12h; Inert atmosphere;

  • 8
  • [ 7299-55-0 ]
  • [ 14316-14-4 ]
  • N-(p-toluenesulfonyl)-2-acetylmethylmorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With triphenylphosphine In acetonitrile at 80℃; for 24h;
  • 9
  • [ 14316-14-4 ]
  • [ 104662-01-3 ]
  • N-(p-toluenesulfonyl)-2-cyclohexanoylmethylmorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With triphenylphosphine In acetonitrile at 80℃; for 24h;
  • 10
  • [ 14316-14-4 ]
  • [ 64819-94-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 65 percent / K2CO3 / dimethylformamide / 24 h / 70 °C 2: 93 percent / pyridine / 0 °C
Multi-step reaction with 3 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / pyridine 3: 82 percent / Gabriel reaction
  • 11
  • [ 14316-14-4 ]
  • [ 76980-45-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 65 percent / K2CO3 / dimethylformamide / 24 h / 70 °C 2: 93 percent / pyridine / 0 °C 4: 57 percent / NaOH / H2O; diethyl ether / 12 h 5: 1.) sodium / 1.) EtOH, 60 deg C, 30 min; 2.) DMF, 100 deg C, 1 h
Multi-step reaction with 5 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / pyridine 3: 82 percent / Gabriel reaction 4: 57 percent / H2O; diethyl ether 5: 1.) NaH / 1) DMF; 2) DMF
  • 12
  • [ 14316-14-4 ]
  • [ 76980-40-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 65 percent / K2CO3 / dimethylformamide / 24 h / 70 °C 2: 93 percent / pyridine / 0 °C 4: 57 percent / NaOH / H2O; diethyl ether / 12 h
Multi-step reaction with 4 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / pyridine 3: 82 percent / Gabriel reaction 4: 57 percent / H2O; diethyl ether
  • 13
  • [ 14316-14-4 ]
  • [ 76980-39-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 65 percent / K2CO3 / dimethylformamide / 24 h / 70 °C 2: 93 percent / pyridine / 0 °C
Multi-step reaction with 2 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / pyridine
  • 14
  • [ 38761-67-0 ]
  • [ 14316-14-4 ]
  • [ 1008757-13-8 ]
YieldReaction ConditionsOperation in experiment
77% With potassium phosphate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 130℃; for 21h;
  • 15
  • [ 1020203-56-8 ]
  • [ 14316-14-4 ]
  • [ 1020203-73-9 ]
YieldReaction ConditionsOperation in experiment
89% With potassium phosphate In N,N-dimethyl-formamide at 110℃; for 3h;
  • 16
  • [ 14316-14-4 ]
  • [ 106-95-6 ]
  • [ 869275-29-6 ]
YieldReaction ConditionsOperation in experiment
79% With potassium carbonate In acetonitrile for 0.166667h; Reflux;
With potassium carbonate In acetone
5.5 g Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 16h;
With potassium carbonate In acetone Reflux;
With potassium carbonate In acetone for 12h; Reflux; Inert atmosphere;
With potassium carbonate In acetone for 2h; Reflux;
With potassium carbonate; potassium iodide In acetone for 16h; Inert atmosphere; Reflux;
Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;

  • 17
  • [ 1125-88-8 ]
  • [ 14316-14-4 ]
  • [ 70509-21-6 ]
YieldReaction ConditionsOperation in experiment
With camphor-10-sulfonic acid In 1,2-dichloro-ethane at 20 - 70℃;
  • 18
  • [ 14316-14-4 ]
  • [ 932-87-6 ]
  • [ 1160723-39-6 ]
YieldReaction ConditionsOperation in experiment
97% With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h;
89% With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h;
56% With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine
With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h;

  • 19
  • [ 14316-14-4 ]
  • [ 123-38-6 ]
  • [ 1190398-17-4 ]
YieldReaction ConditionsOperation in experiment
81% With amberlyst-15 In dichloromethane at 20℃; for 2h; Inert atmosphere; Molecular sieve;
  • 22
  • [ 142-26-7 ]
  • [ 98-59-9 ]
  • [ 16180-96-4 ]
  • [ 14316-14-4 ]
  • 1-O-acetyl-2-(tosylamido)ethanol [ No CAS ]
  • 23
  • [ 141-43-5 ]
  • [ 2232-08-8 ]
  • [ 14316-14-4 ]
  • 24
  • [ 5117-12-4 ]
  • [ 14316-14-4 ]
  • [ 1265900-15-9 ]
YieldReaction ConditionsOperation in experiment
39% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 30℃; for 3h; Inert atmosphere;
  • 25
  • [ 2680-03-7 ]
  • [ 14316-14-4 ]
  • [ 1265900-26-2 ]
YieldReaction ConditionsOperation in experiment
67% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 17h; Inert atmosphere;
  • 26
  • [ 1663-39-4 ]
  • [ 14316-14-4 ]
  • [ 1265900-22-8 ]
YieldReaction ConditionsOperation in experiment
72% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 6h; Inert atmosphere;
  • 27
  • [ 2210-25-5 ]
  • [ 14316-14-4 ]
  • [ 1265900-28-4 ]
YieldReaction ConditionsOperation in experiment
38% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 17h; Inert atmosphere;
  • 28
  • [ 5535-48-8 ]
  • [ 14316-14-4 ]
  • [ 1265900-17-1 ]
YieldReaction ConditionsOperation in experiment
65% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 24h; Inert atmosphere;
  • 29
  • [ 14316-14-4 ]
  • [ 78-94-4 ]
  • [ 1265900-29-5 ]
YieldReaction ConditionsOperation in experiment
53% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 30℃; for 8h; Inert atmosphere;
  • 30
  • [ 14316-14-4 ]
  • [ 107-13-1 ]
  • [ 1265900-31-9 ]
YieldReaction ConditionsOperation in experiment
18% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 120h; Inert atmosphere;
  • 31
  • [ 14316-14-4 ]
  • [ 292638-85-8 ]
  • [ 1265900-20-6 ]
YieldReaction ConditionsOperation in experiment
83% With dipotassium peroxodisulfate; palladium diacetate; toluene-4-sulfonic acid In toluene at 20℃; for 16h; Sealed tube; 4.3. General procedure for the synthesis of benzoxazines General procedure: An oven-dried stoppered round-bottom flask was charged with Pd(OAc)2 (10 mol%), sulfonamide (0.19 mmol), p-TsOH (108 mg, 0.57 mmol) and potassium persulfate (513 mg, 1.9 mmol) in 3mL of dry toluene. The reaction mixture was stirred for 5 min temperature, and then alkene (0.49 mmol) was added and stirred for 16 h at room temperature. The resulting dark brown reaction mixture was titrated with water (10 mL) and extracted with ethyl acetate (3 x 10 mL). The combine organic layer was dried over anhydrous sodium sulfate and solvent was removed under reduced pressure. The crude reaction mixture was purified by column chromatography over silica gel using mixture of ethyl acetate and petroleum ether (10: 90) as eluent.
79% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 6h; Inert atmosphere;
  • 32
  • [ 14316-14-4 ]
  • [ 79-10-7 ]
  • [ 1265900-24-0 ]
YieldReaction ConditionsOperation in experiment
60% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 6h; Inert atmosphere;
  • 33
  • [ 14316-14-4 ]
  • [ 193634-77-4 ]
  • [ 1265900-13-7 ]
YieldReaction ConditionsOperation in experiment
54% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 24h; Inert atmosphere;
  • 34
  • [ 14316-14-4 ]
  • [ 70-11-1 ]
  • [ 1346694-44-7 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In acetone at 20℃;
  • 35
  • [ 14316-14-4 ]
  • [ 598-31-2 ]
  • [ 1346694-38-9 ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate In acetone at 20℃;
  • 36
  • [ 141-43-5 ]
  • [ 98-09-9 ]
  • [ 14316-14-4 ]
YieldReaction ConditionsOperation in experiment
91% With cesium fluoride supported on Celite at 50℃; chemoselective reaction;
  • 37
  • [ 1458-98-6 ]
  • [ 14316-14-4 ]
  • N-(2-hydroxyethyl)-4-methyl-N-(2-methylallyl)-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate In acetone Reflux;
73% With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere;
56% With potassium carbonate; potassium iodide In acetone for 16h; Reflux;
With potassium carbonate; potassium iodide In acetone at 20℃; Reflux;
With potassium carbonate In acetone Reflux;

  • 38
  • [ 1265015-72-2 ]
  • [ 14316-14-4 ]
  • [ 1415811-08-3 ]
YieldReaction ConditionsOperation in experiment
74% With Tri(p-tolyl)phosphine In dichloromethane for 48h; Inert atmosphere; Reflux;
  • 39
  • [ 1242071-56-2 ]
  • [ 14316-14-4 ]
  • [ 1415811-15-2 ]
YieldReaction ConditionsOperation in experiment
81% With Tri(p-tolyl)phosphine In dichloromethane for 48h; Inert atmosphere; Reflux;
  • 40
  • [ 2002-24-6 ]
  • [ 98-59-9 ]
  • [ 14316-14-4 ]
  • 41
  • [ 14316-14-4 ]
  • [ 768-03-6 ]
  • N-(2-hydroxyethyl)-4-methyl-N-(3-oxo-3-phenylpropyl) benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 20℃; for 24h;
  • 42
  • [ 14316-14-4 ]
  • [ 3634-89-7 ]
YieldReaction ConditionsOperation in experiment
95% With Nonafluorobutanesulfonyl fluoride; triethylamine In dichloromethane at 20℃; for 1h; The general procedure for the RfSO2F-induced cyclodehydration of b-hydroxysulfonamide to the corresponding aziridine General procedure: At room temperature, n-C4F9SO2F(4.0 mmol, 2.0 M equiv) was slowly added via syringe to a solution of bhydroxysulfonamide (2.0 mmol) and Et3N (6.0 mmol, 3.0 M equiv) in CH2Cl2,and the resulting mixture was stirred at room temperature for 1-2 h. Afterevaporation of the reaction mixture to remove volatile components, theresidue obtained was purified through silica gel column chromatography(petroleum:ethyl acetate = 10:1, v/v), providing the corresponding aziridine inthe yields of 61-95%.
Multi-step reaction with 2 steps 1: iodine; triphenylphosphine; 1H-imidazole / acetonitrile; diethyl ether / 12 h / 0 - 20 °C 2: ferric(III) bromide; 1,10-Phenanthroline / acetonitrile / 0.5 h / 60 °C
  • 43
  • [ 100-42-5 ]
  • [ 14316-14-4 ]
  • [ 321977-41-7 ]
  • [ 1265900-10-4 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; silver trifluoromethanesulfonate In dichloromethane at 25℃; for 1h; Inert atmosphere; Schlenk technique; Overall yield = 65 %; Overall yield = 62 mg; stereoselective reaction;
With toluene-4-sulfonic acid; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane; water at 25℃; for 4h; Inert atmosphere; Schlenk technique; Overall yield = 58 %; Overall yield = 61 mg; 4.2. PhI(OCOCF3)2 Mediated synthesis of oxazolidines 3ae-3ag: Method A General procedure: 4.2.1. General procedure for the PhI(OCOCF3)2 mediated synthesis of oxazolidines 3ae3ag: Method A. To a colorless solution of corresponding N-Ts aminoalcohol (0.33 mmol) and styrene (0.36 mmol) in CH2Cl2 (3 mL) in a well dried Schlenk flask under argon atmosphere was added PhI(OCOCF3)2 (0.50 mmol) and PTSA*H2O (0.36 mmol) at room temperature [25 °C]. The progress of the reaction was monitored by TLC. After stirring the reaction mixture for 4 h at room temperature 5 mL of satd soln of aq NaHCO3 was added and extracted with CH2Cl2. The combined organic layers were dried (anhyd. Na2SO4), filtered and concentrated in vacuo. The crude product obtained was purified by flash chromatography (pet. ether : Et2O, 8:1) to furnish oxazolidines in pure form.
  • 44
  • [ 51010-88-9 ]
  • [ 202974-92-3 ]
  • [ 14316-14-4 ]
  • [ 1579963-97-5 ]
YieldReaction ConditionsOperation in experiment
47% Stage #1: N-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-benzenesulfonamide With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.5h; Inert atmosphere; Stage #2: methyl (2E,4E)-6-bromo-2,4-hexadienoate In tetrahydrofuran; mineral oil at 20℃; for 20h; Inert atmosphere; Stage #3: With acetic acid In tetrahydrofuran; water at 20℃; for 18h; Inert atmosphere;
  • 45
  • [ 14316-14-4 ]
  • [ 106-96-7 ]
  • 4-methyl-N-(2-(prop-2-yn-1-yloxy)ethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: propargyl bromide In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃;
  • 46
  • [ 3360-54-1 ]
  • [ 14316-14-4 ]
  • N-(2-hydroxyethyl)-4-methyl-N-(2-phenylallyl)-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere;
66% With potassium carbonate; potassium iodide In acetone at 60℃;
With potassium carbonate In acetone Reflux;
  • 47
  • [ 20038-12-4 ]
  • [ 14316-14-4 ]
  • N-(2-hydroxyethyl)-4-methyl-N-(3-methylbut-3-en-1-yl)-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere;
  • 48
  • [ 36963-70-9 ]
  • [ 14316-14-4 ]
  • N-(2-hydroxyethyl)-4-methyl-N-(3-phenylbut-3-en-1-yl)-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere;
  • 49
  • [ 14316-14-4 ]
  • [ 82017-87-6 ]
  • N-(2-((1,3-diphenyl-1,3,2-diazaphospholidin-2-yl)oxy)ethyl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;
With triethylamine In dichloromethane at 0 - 20℃; for 2h;
With triethylamine In dichloromethane at 0 - 20℃; for 4h;

  • 50
  • [ 14316-14-4 ]
  • [ 106-96-7 ]
  • [ 317842-46-9 ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate In acetone at 85℃; for 12h; Inert atmosphere;
99% With potassium carbonate In acetone for 12h; Schlenk technique; Inert atmosphere; Heating;
With potassium carbonate In acetone for 2h; Reflux;
  • 51
  • [ 14316-14-4 ]
  • C16H15(2)HO3S [ No CAS ]
  • C18H20(2)HNO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 5h;
  • 52
  • [ 14316-14-4 ]
  • [ 16714-25-3 ]
  • [ 536-74-3 ]
  • 4-methyl-N-(2-((2-phenylquinolin-4-yl)oxy)ethyl)-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; chemoselective reaction;
  • 53
  • [ 2270-59-9 ]
  • [ 14316-14-4 ]
  • N-(2-hydroxyethyl)-4-methyl-N-(4-methylpent-3-en-1-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate; potassium iodide In acetone for 16h; Reflux;
45% With potassium carbonate; potassium iodide In acetone at 60℃; Schlenk technique; Inert atmosphere;
  • 54
  • [ 74-85-1 ]
  • [ 768-32-1 ]
  • [ 14316-14-4 ]
  • 4-methyl-N-(2-phenethoxyethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With (triphenylphosphine)gold(I) chloride; 1-(trifluoromethanesulfonyloxy)-1,2-benziodoxol-3(1H)-one In acetonitrile at 50℃; for 18h; Sealed tube;
  • 55
  • [ 14316-14-4 ]
  • [ 3981-23-5 ]
YieldReaction ConditionsOperation in experiment
94% With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0℃; for 3h; Inert atmosphere;
With 1H-imidazole; iodine; triphenylphosphine In diethyl ether; acetonitrile at 0 - 20℃; for 12h; Typical procedure for the synthesis of starting materials General procedure: Iodination: To a solution of triphenylphosphine (1.97 g, 7.5 mmol, 3.0 equiv) and imidazole (0.58 g, 8.5 mmol, 3.4 equiv) in Et2O:CH3CN = 3:1 (25 mL) was added I2 (1.90 g, 7.5 mmol, 3.0 equiv) slowly at 0 oC. After stirred for 30 minutes, add N-tosylated alcohol (2.5 mmol) to the solution dropwise. The mixture was stirred for 12 hours at room temperature. Check the progress of the reaction by TLC, the reaction mixture was quenched with saturated NH4Cl aqueous solution and extracted by CH2Cl2. The organic layer was dried over MgSO4 and concentrated under the vacuum. Flash column chromatography provided the iodinated products.
  • 56
  • [ 14316-14-4 ]
  • [ 106-99-0 ]
  • [ 1361844-07-6 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With copper diacetate; palladium diacetate In dimethyl sulfoxide at 20℃; for 0.25h; Sealed tube; Stage #2: buta-1,3-diene With oxygen In dimethyl sulfoxide at 80℃; for 24h; Sealed tube;
  • 57
  • [ 14316-14-4 ]
  • [ 513-81-5 ]
  • 3-methyl-3-(prop-1-en-2-yl)-4-tosylmorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With copper diacetate; palladium diacetate In dimethyl sulfoxide at 20℃; for 0.25h; Sealed tube; Stage #2: 2,3-dimethyl-buta-1,3-diene With oxygen In dimethyl sulfoxide at 80℃; for 24h; Sealed tube;
  • 58
  • [ 29414-55-9 ]
  • [ 14316-14-4 ]
  • 3-(4-(3,3-dimethyloxiran-2-yl)but-1-en-2-yl)-4-tosylmorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With copper diacetate; palladium diacetate In dimethyl sulfoxide at 20℃; for 0.25h; Sealed tube; Stage #2: 6,7-epoxymyrcene With oxygen In dimethyl sulfoxide at 80℃; for 24h; Sealed tube;
  • 59
  • [ 1515-78-2 ]
  • [ 14316-14-4 ]
  • (E)-3-styryl-4-tosylmorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With copper diacetate; palladium diacetate In dimethyl sulfoxide at 20℃; for 0.25h; Sealed tube; Stage #2: buta-1,3-dien-1-ylbenzene With oxygen In dimethyl sulfoxide at 80℃; for 24h; Sealed tube;
  • 60
  • [ 30448-78-3 ]
  • [ 14316-14-4 ]
  • (E)-3-(4-methoxystyryl)-4-tosylmorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With copper diacetate; palladium diacetate In dimethyl sulfoxide at 20℃; for 0.25h; Sealed tube; Stage #2: p-methoxyphenylbutadiene With oxygen In dimethyl sulfoxide at 80℃; for 24h; Sealed tube;
  • 61
  • [ 14316-14-4 ]
  • [ 79725-96-5 ]
  • (E)-3-(4-bromostyryl)-4-tosylmorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With copper diacetate; palladium diacetate In dimethyl sulfoxide at 20℃; for 0.25h; Sealed tube; Stage #2: 1-bromo-4-(buta-1,3-dienyl)benzene With oxygen In dimethyl sulfoxide at 80℃; for 24h; Sealed tube;
  • 62
  • [ 37677-17-1 ]
  • [ 14316-14-4 ]
  • N-(cyclohex-1-en-1-ylmethyl)-N-(2-hydroxyethyl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In acetone at 20℃;
  • 63
  • [ 14316-14-4 ]
  • [ 1590449-58-3 ]
  • N-benzoyl-O-[α-(N-tosyl-2-aminoethoxy)phenylacetyl]-L-threonine isopropyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With silver trifluoromethanesulfonate In neat (no solvent) at 20℃; for 10h; Inert atmosphere; stereoselective reaction;
98 % ee With silver trifluoromethanesulfonate In neat (no solvent) at 20℃; for 10h; Inert atmosphere; stereoselective reaction;
  • 64
  • [ 14316-14-4 ]
  • 3-bromo-1-iodo-(E)-1-propene [ No CAS ]
  • (E)-N-(2-hydroxyethyl)-N-(3-iodoallyl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;
  • 65
  • [ 14316-14-4 ]
  • [ 78461-58-2 ]
  • (E)-N-(2-hydroxyethyl)-N-(5-iodopent-4-en-1-yl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;
  • 66
  • [ 14316-14-4 ]
  • [ 57483-27-9 ]
YieldReaction ConditionsOperation in experiment
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 3h; General procedure for oxidation of alcohols General procedure: To a solution of primary alcohol in anhydrous DCM was added Dess-Martin periodinane(1.5 equiv) at 0 °C. After being stirred at room temperature for 3 h, the mixture wastreated with saturated aqueous Na2SO3 and NaHCO3. The aqueous layer was extractedwith EtOAc twice. The combined organic layers were washed with brine, dried overMgSO4, and concentrated in vacuo. The residue was purified by silica gel columnchromatography to afford aldehyde.
  • 67
  • [ 14316-14-4 ]
  • [ 95895-33-3 ]
  • N-((4-fluorophenyl)ethynyl)-N-(2-hydroxyethyl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h;
  • 68
  • [ 33675-41-1 ]
  • [ 14316-14-4 ]
  • N-(2-hydroxyethyl)-N-((4-methoxyphenyl)ethynyl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h;
  • 69
  • [ 33491-05-3 ]
  • [ 14316-14-4 ]
  • N-(2-hydroxyethyl)-4-methyl-N-(p-tolylethynyl)-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h;
  • 70
  • [ 33675-43-3 ]
  • [ 14316-14-4 ]
  • N-(2-hydroxyethyl)-4-methyl-N-(m-tolylethynyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h;
  • 71
  • [ 14316-14-4 ]
  • [ 72591-20-9 ]
  • N-(2-hydroxyethyl)-4-methyl-N-(o-tolylethynyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium carbonate In toluene at 80℃; for 12h; Inert atmosphere;
  • 72
  • [ 14316-14-4 ]
  • C8H14N2O5S [ No CAS ]
  • ethyl 2-diazo-5-((N-(2-hydroxyethyl)-4-methylphenyl)sulfonamido)pentanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 8h;
  • 73
  • [ 14316-14-4 ]
  • [ 55759-12-1 ]
  • 4-N-tosyl-2-vinylmorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With bis(η3-allyl-μ-chloropalladium(II)); Methyl formate; triethylamine; bis[2-(diphenylphosphino)phenyl] ether In water; toluene at 45℃; for 21h; Sealed tube; Inert atmosphere; Schlenk technique;
  • 74
  • [ 14316-14-4 ]
  • 1-(1-(4-methoxyphenyl)vinyl)tetrahydro-1H-thiophen-1-ium triflate [ No CAS ]
  • 2-(4-methoxyphenyl)-4-tosylmorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With caesium carbonate In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Schlenk technique; Stage #2: 1-(1-(4-methoxyphenyl)vinyl)tetrahydro-1H-thiophen-1-ium triflate In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique;
  • 75
  • [ 405-99-2 ]
  • [ 14316-14-4 ]
  • 2-(4-fluorobenzyl)-3-tosyloxazolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique;
  • 76
  • [ 1073-67-2 ]
  • [ 14316-14-4 ]
  • 2-(4-chlorobenzyl)-3-tosyloxazolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique;
  • 77
  • [ 2039-82-9 ]
  • [ 14316-14-4 ]
  • 2-(4-bromobenzyl)-3-tosyloxazolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique;
  • 78
  • [ 622-97-9 ]
  • [ 14316-14-4 ]
  • 2-(4-methylbenzyl)-3-tosyloxazolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique;
  • 79
  • [ 1746-23-2 ]
  • [ 14316-14-4 ]
  • 2-(4-(tert-butyl)benzyl)-3-tosyloxazolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique;
  • 80
  • [ 637-69-4 ]
  • [ 14316-14-4 ]
  • 2-(4-methoxybenzyl)-3-tosyloxazolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique;
  • 81
  • [ 402-50-6 ]
  • [ 14316-14-4 ]
  • 3-tosyl-2-(4-(trifluoromethyl)benzyl)oxazolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique;
  • 82
  • [ 2350-89-2 ]
  • [ 14316-14-4 ]
  • 2-([1,1'-biphenyl]-4-ylmethyl)-3-tosyloxazolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique;
  • 83
  • [ 827-54-3 ]
  • [ 14316-14-4 ]
  • 2-(naphthalen-2-ylmethyl)-3-tosyloxazolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique;
  • 84
  • [ 611-15-4 ]
  • [ 14316-14-4 ]
  • 2-(2-methylbenzyl)-3-tosyloxazolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique;
  • 85
  • [ 2039-87-4 ]
  • [ 14316-14-4 ]
  • 2-(2-chlorobenzyl)-3-tosyloxazolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique;
  • 86
  • [ 2039-88-5 ]
  • [ 14316-14-4 ]
  • 2-(2-bromobenzyl)-3-tosyloxazolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique;
  • 87
  • [ 350-51-6 ]
  • [ 14316-14-4 ]
  • 2-(3-fluorobenzyl)-3-tosyloxazolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique;
Same Skeleton Products
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Sulfamides

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