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Product Details of [ 404-24-0 ]

CAS No. :404-24-0 MDL No. :MFCD00196027
Formula : C8H6F3NO Boiling Point : -
Linear Structure Formula :- InChI Key :SAPQIENQEZURNZ-UHFFFAOYSA-N
M.W : 189.13 Pubchem ID :67881
Synonyms :

Calculated chemistry of [ 404-24-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.95
TPSA : 29.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 2.21
Log Po/w (WLOGP) : 3.26
Log Po/w (MLOGP) : 2.0
Log Po/w (SILICOS-IT) : 1.94
Consensus Log Po/w : 2.17

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.55
Solubility : 0.535 mg/ml ; 0.00283 mol/l
Class : Soluble
Log S (Ali) : -2.46
Solubility : 0.662 mg/ml ; 0.0035 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.29
Solubility : 0.0979 mg/ml ; 0.000518 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 404-24-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 404-24-0 ]

* 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 [ 404-24-0 ]

[ 404-24-0 ] Synthesis Path-Downstream   1~101

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YieldReaction ConditionsOperation in experiment
63% With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate; at 96 - 100℃; for 2h; General procedure: A mixture of amine (0.02 mol), acetic acid (0.025 mol, 1.5 mL) and [BMIM(SO3H)][OTf] (50 mol %) was charged in an oven-dried round bottom flask and the reaction mixture was refluxed on an oil bath. Progress of the reaction was monitored by TLC and by GC-MS. After completion of reaction, the reaction mass was cooled at room temperature and poured into ice water. The crystals of N-acylated product so obtained were filtered, washed with of cold ethanol-water mixture (10-15 mL) and dried. The purity of all the products was checked by TLC and GC, and all the pure products were characterized by IR, GC-MS/LC-MS, 1HNMR and 13CNMR. The filtrate (water + ethanol + IL) was set aside for recovery and reuse of the IL.
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YieldReaction ConditionsOperation in experiment
68% With triethylamine; In dichloromethane; at 0 - 20℃; for 2h; Aniline (5mL, 0.055mol) and Et3N (7.7mL, 0.055mol) was dissolved in dry CH2Cl2 (20mL). The mixture was cooled to 0C and then was TFAA (7.6mL, 0.055mol) slowly added. The reaction was allowed to reach rt. and stirred for 2h. The CH2Cl2 was evaporated and the mixture dissolved in EtOAc and transferred to a separatory funnel. The organic phase was washed thrice with 1M HCl solution, then saturated sodium bicarbonate solution and brine. The organic phase was dried over MgSO4 and evaporated to dryness. The solid was recrystallized from pentane/Et2O giving white fluffy crystals. 7.02g, 68%, Rf 0.32 (pentane/EtOAc 10:1) Mp 86.2-89.2C, lit. 87.7C [19]. 1H NMR (400MHz, CDCl3) deltaH 7.85 (s, 1H, NH), 7.45 (d, J 7.7Hz, 2H), 7.28 (t, J 8.0Hz, 2H), 7.14 (t, J 7.4Hz, 1H). 13C NMR (100MHz, CDCl3) deltaC 155.3 (q, JC-F 37.5Hz, C=O), 135.2, 129.4, 126.5, 120.9, 115.9 (q, JC-F 288.4Hz, CF3). 19F NMR (376MHz, CDCl3) deltaF-75.7. HRMS (ES): calcd. for C8H6F3NONa+ 212.0294; found 212.0288. Spectral values were in accordance with those reported in Ref.[19].
With triethylamine; In dichloromethane; at -78 - 20℃; Under an N2 atmosphere at -78 C., 2,2,2-trifluoroacetic anhydride (1 equivalent) was added drop wise to a solution of the aniline (1 equivalent), triethylamine (1 equivalent), and CH2Cl2 (0.6 M). The reaction was allowed to warm to RT over a period of 30 minutes. After evaporating the solvents under reduced pressure, purification via silica gel chromatography using 7/3 hexanes/EtOAc gave desired product.
In acetone; at 20℃; 83.8 g of aniline was dissolved in 405 ml of acetone,Control internal temperature 0 10 ,Add 189 g of trifluoroacetic anhydride dropwise,After the addition,Naturally rise to room temperature until the reaction is complete,The reaction solution was concentrated to dryness and dissolved in 180 ml of acetonitrile and stored for future use.
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  • diethyl 2,2,2-trifluoro-N-phenylacetamidoyl phosphite [ No CAS ]
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  • 1-anilino-2-methyl-4,6-diphenylpyridinium tetrafluoroborate [ No CAS ]
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  • 1-phenyl-1-(N-phenylimino)-3-(N-phenylamino)-4,4,4-trifluoro-2-butene [ No CAS ]
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  • 1-anilino-2-methyl-4,6-diphenylpyridinium tetrafluoroborate [ No CAS ]
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YieldReaction ConditionsOperation in experiment
43% With bismuth (III) nitrate pentahydrate; acetic anhydride; In dichloromethane; at 23℃; General procedure: A flame-dried reaction vessel with a magnetic stirring bar was charged with substrate (0.2mmol), Bi(NO3)3?5H2O (97 mg, 0.2 mmol), dichloromethane (1 mL), and Ac2O (114 muL,1.2 mmol) in sequence. The mixture was stirred at room temperature under airfor 2.5-5 h and cooled to room temperature. After completion of the reaction, the mixture wasquenched with solution of saturated NaHCO3.The resulting mixture was extracted with ethyl acetate (3×20 mL). The combined organic layer wasdried with Na2SO4 and then concentrated under vacuum. Afterevaporation, the residue was purified by column chromatography using silica gel(300-400 mesh size) and petroleum ether / EtOAc as the eluent.
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  • N-[(Dimethyl-phenyl-silanyl)-methyl]-2,2,2-trifluoro-N-phenyl-acetamide [ No CAS ]
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  • N2-Phenylbenzamidin-N2-ium trifluoroacetate [ No CAS ]
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YieldReaction ConditionsOperation in experiment
61% With triethylamine; dichlorotriphenylphosphorane; In acetonitrile; for 3h;Reflux; N-Phenyltrifluoroacetamide [18] (4.00 g, 21.2 mmol) anddichlorotriphenylphosphorane (17.6 g, 52.9 mmol) were suspendedin MeCN (80 ml) and Et3N (7.67 ml, 55.0 mmol) was added. Thesuspension was refluxed for 3 h and then cooled to 0 C. Theprecipitated solids (Et3N.HCl and Ph3PO) were removed by filtrationand the filtrate concentrated under reduced pressure. The residue was dissolved in minimal CHCl3 and triturated with hexanes.The precipitate was removed by filtration and the filtrateconcentrated under reduced pressure. The residue was purified byflash chromatography (Et2O/hexanes 1:4) afford the chloride as acolourless liquid (2.68 g, 61%). 1H NMR (500 MHz, CDCl3)d 7.48e7.40 (m, 2H), 7.34e7.28 (m, 1H), 7.13e7.07 (m, 2H); 13C NMR(125 MHz, CDCl3) d 143.6, 132.1 (q, J 277.1 Hz), 129.3, 127.6, 120.8,117.0 (q, J 43.0 Hz); IR (acetone) 1506, 1260, 1093, 1055, 1012, 795,693 cm1; HRMS (ESI) calcd for C8H6ClF3N [MH] 208.0135,found 208.0136.
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  • S,S-dimethylanilinosulfonium picrate [ No CAS ]
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  • GENERIC INORGANIC CATION; trifluoro-acetate [ No CAS ]
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YieldReaction ConditionsOperation in experiment
1.4 Analogously to Example 1.1, 5.0 ml of aniline give 10.25 g of N-phenyl-2,2,2-trifluoroacetamide ("BA"), FAB 190.
12.1 Preparation of N-trifluoroethylaniline derivative To a suspension of 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]aniline (9.07 g, 35.0 mmol) in CH2Cl2 (100 mL) was added a solution of trifluoroacetic anhydride (5.7 mL, 40.2 mmol) in CH2Cl2 (50 mL) dropwise at room temperature. The solution was stirred for 3 hours (solution cleared and TLC indicated that the reaction was completed. The reaction mixture was washed with water, aqueous NaHCO3, and brine. The organic layer was drawn off, dried over MgSO4, filtered, and concentrated to give 12.1 g of the intermediate trifluoroacetanilide (12.1a). The intermediate 12.1a was taken up in THF (50 mL) and treated with LiAlH4 (4.00 g, 106 mmol) at reflux for 10 hours.
EXAMPLE 9 General Synthesis of N-trifluoroacetylaminobenzenes To a stirred solution of the aniline (2.00 mmol) and pyridine (0.18 mL, 2.22 mmol, 1.1 eq) in anhydrous methylene chloride (10 mL) at 0 C. under a nitrogen atmosphere is added dropwise trifluoroacetic anhydride (0.31 mL, 2.19 mmol, 1.1 eq). The resultant reaction mixture is stirred at 0 C. under a nitrogen atmosphere for 3 hours. Water is added (15 mL), and this aqueous mixture is extracted with ethyl acetate (3*15 mL). The extracts are combined, dried (mgSO4), and evaporated under reduced pressure. If necessary, the residue is column chromatographed using silica gel (approximately 50 g) and elution with an ethyl acetate gradient in hexanes to afford the corresponding N-trifluoroacetylaminobenzene. Using this procedure the following compound was prepared:
EXAMPLE 3 Fluorination of N-trifluoroacetylaniline A solution of 9.5 parts of N-trifluoroacetylaniline in 740 parts of chloroform was cooled to 0 C. and fluoroxytrifluoromethane was added at a rate of 4.31 parts/hr for 2 hours. Gas chromatographic analysis of the reaction product indicated 4% unreated N-trifluoroacetylaniline, 44% N-trifluoroacetyl-2-fluoroaniline, 11% N-trifluoroacetyl-4-fluoroaniline, 3% N-trifluoroacetyl-2,4-di-fluoroaniline, 8% N-trifluoroacetyl-2,6-difluoroaniline, and 1% N-trifluoroacetyl-2,4,6-trifluoroaniline.
STEP A: 2,2,2-trifluoro-N-phenyl-acetamide Using the procedure of Step A of Example 8, aniline was reacted to obtain 2,2,2-trifluoro-N-phenyl-acetamide melting at 85 C. which after crystallization from petroleum ether (b.p.=60-80 C.) melted at 87 C.

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  • 2,2,2-trifluoro-N-(4-iodophenyl)-N-phenylacetamide [ No CAS ]
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  • (R)-2-(N-phenyl-N-trifluoroacetyl)aminopropionic acid ethyl ester [ No CAS ]
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  • <i>N</i>-[3-(1-allyl-9<i>H</i>-carbazol-2-yloxy)-propyl]-2,2,2-trifluoro-<i>N</i>-phenyl-acetamide [ No CAS ]
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  • 2,2,2-trifluoro-1-(2-phenylaminophenyl)ethanone [ No CAS ]
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  • 1-(2-phenylamino-4-methoxyphenyl)trifluoroethanone [ No CAS ]
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  • {2,2,2-Trifluoro-1-[(Z)-phenylimino]-ethyl}-phosphonic acid dimethyl ester [ No CAS ]
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  • S,S-dimethylanilinosulfonium picrate [ No CAS ]
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  • (Z)-2,2,2-trifluoro-N-phenylacetimidoyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.2% With triethylamine; chlorophosphoric acid diphenyl ester; In acetonitrile; at 82℃; for 15h; Example 1 N-phenyl-2,2,2-trifluoroacetimidoyl chloride Seven grams (37.0 mmol) of <strong>[404-24-0]2,2,2-trifluoro-N-phenylacetamide</strong>, 19.84 g (74.0 mmol) of diphenyl chlorophosphate, 7.44 g (74.0 mmol) of triethylamine, and 28 ml of acetonitrile were introduced into a 100 ml flask and reacted for 15 hours while being refluxed (82C). After the reaction, the reaction solution was cooled to room temperature, 28 ml of ethyl acetate was added thereto, and the precipitate was then filtered off. The filtrate was subjected to solvent removal by evaporation, and the crude product thus obtained was purified by column chromatography (silica gel, ethyl acetate:hexane = 3:7), resulting in 6.24 g of N-phenyl-2,2,2-trifluoroacetimidoyl chloride as a yellow liquid (yield: 81.2%). IR (neat, cm-1): 1697, 1489, 1286, 1223, 1196, 1161, 947, 766, 725, 691 1H-NMR (CDCl3): delta 7.41-7.24 (m, 3H), 7.08-7.05(m, 2H) 13C-NMR (CDC13): delta 143. 47, 131.94 (q, J = 42.8 Hz), 129.12, 127.40, 120.63, 116.86 (q, J = 275.8 Hz)
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  • o-bromotrifluoroacetanilide [ No CAS ]
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YieldReaction ConditionsOperation in experiment
With potassium hydroxide; methyllithium; In tetrahydrofuran; methanol; diethyl ether; pentane; ii) A solution of o-bromotrifluoroacetanilide (325 mg, 1.2 mM) in tetrahydrofuran (THF)(20 cm3) was cooled to -78 C. and to this was added methyl lithium (1 molar equivalent of a 1.4 M solution in diethyl ether). This addition was followed 10 minutes later by the introduction of tert-butyllithium (2 molar equivalent of a 1.7 M solution in pentane). The reaction mixture was stirred for 1 hour at -78 C., and then a solution of the chloroindanone (272 mg. 1.2 mM) in THF (3 cm3) added dropwise via a cannula. The solution was allowed to warm slowly to room temperature, and stirred for one hour, then a 10% solution potassium hydroxide in methanol (3 cm3) was introduced. After stirring for 30 minutes, the reaction mixture was poured into 2 M HCl, and extracted with dichloromethane (3 *10 cm3). The combined organic extracts were dried (Na2 SO4) and evaporated in vacuo to afford a solid residue which was chromatographed on silica, eluding with 10% ethyl acetate/petroleum ether (60-80 C.) to yield trifluoroacetanilide (RF 0.4)(50 mg), and the 2-chloro-1-hydroxy-5-methoxy-4,6-dimethyl-1-(2'-trifluoroacetamidophenyl)indane (RF 0.3) (220 mg, 44%).
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YieldReaction ConditionsOperation in experiment
With sodium bicarbonate; bromine; In methanol; water; EXAMPLE 8 General Synthesis of 2-Halo-N-trifluoroacetylanilines To a stirred mixture of the N-trifluoroacetylaniline (2.00 mmol) and sodium hydrogen carbonate (0.21 g, 2.50 mmol, 1.25 eq) in methanol (10 mL) at 0 C. is added dropwise bromine (0.113 mL, 2.19 mmol, 1.1 eq). The resulting reaction mixture is then stirred at 25 C. for 30 minutes. The reaction mixture is then evaporated under reduced pressure, and the residue is placed in water made acidic to pH 3 with HCI (10 mL). This aqueous mixture is extracted with ethyl acetate (3*15 mL). The extracts is combined, dried (MgSO4), and evaporated under reduced pressure. The residue is column chromatographed using silica gel (approximately 50 g) and elution with an appropriate solvent system to afford the corresponding 2-bromo-N-trifluoroacetylaniline. Using this procedure, the following compound was prepared:
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  • [ 404-24-0 ]
YieldReaction ConditionsOperation in experiment
99% In chloroform; at 42℃; for 5h; A solution of 2-(2-aminobenzoyl)pyridine (1.29 g, 6.32 mmol, Syn. Comm. 1996, 26, 721-727) and trifluroacetic anhydride (1.10 mL, 7.79 mmol) in CHCl3 (35 mL) was heated at 42 C for 5 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc (ca. 250 mL), washed with saturated aqueous NaHCO3 (2 x 50 mL), H2O (1 x 50 mL), brine (1 x 50 mL), dried (Na2SO4) and concentrated under reduced pressure to give 1.91 g (99%) of the trifluoracetanilide. A mixture of KNO3 (905 mg, 8.96 mmol) in concentrated H2SO4 (12 mL) was added to a mixture of amide (1.76 g, 5.97 mmol) in concentrated H2SO4 (18mL) maintaining the reaction temperature at ? 16 C with an ice bath. The reaction mixture was allowed to warm to room temperature, stirred 4 h, and poured onto ice (ca. 150 g). The mixture was neutralized by slow addition of 25% aqueous NaOH (ca. 175 mL) maintaining the temperature at ? 18 C with an ice bath. The aqueous layer was extracted with EtOAc (2 x 200 mL). The combined organic extracts were washed with H2O (1 x 100 mL), brine (1 x 100 mL), dried (Na2SO4) and concentrated under reduced pressure to give a solid. Purification by flash chromatography, elution with 20% EtOAc-hexane, to provide 1.19 g (59%) of the 4-nitro-trifluoracetanilide compound as a yellow solid. A mixture of the nitro compound prepared as above (1.14 g, 3.36 mmol), MeOH (33 mL), and H2O (13mL) was treated with K2CO3 (2.32 g, 16.8 mmol) and heated at reflux for 2h. The reaction mixture was cooled to room temperature and MeOH was removed under reduced pressure. The aqueous residue was extracted with EtOAc (2 x 200 mL). The combined organic extracts were washed with H2O (1 x 100 mL), brine (1 x 100 mL), dried (Na2SO4) and concentrated under reduced pressure to give Int-4, in quantitative yield, as a yellow solid.
  • 84
  • [ 404-24-0 ]
  • [ 404-27-3 ]
YieldReaction ConditionsOperation in experiment
59% A solution of 2-(2-aminobenzoyl)pyridine (1.29 g, 6.32 mmol, Syn. Comm. 1996, 26, 721-727) and trifluroacetic anhydride (1.10 mL, 7.79 mmol) in CHCl3 (35 mL) was heated at 42 C for 5 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc (ca. 250 mL), washed with saturated aqueous NaHCO3 (2 x 50 mL), H2O (1 x 50 mL), brine (1 x 50 mL), dried (Na2SO4) and concentrated under reduced pressure to give 1.91 g (99%) of the trifluoracetanilide. A mixture of KNO3 (905 mg, 8.96 mmol) in concentrated H2SO4 (12 mL) was added to a mixture of amide (1.76 g, 5.97 mmol) in concentrated H2SO4 (18mL) maintaining the reaction temperature at ? 16 C with an ice bath. The reaction mixture was allowed to warm to room temperature, stirred 4 h, and poured onto ice (ca. 150 g). The mixture was neutralized by slow addition of 25% aqueous NaOH (ca. 175 mL) maintaining the temperature at ? 18 C with an ice bath. The aqueous layer was extracted with EtOAc (2 x 200 mL). The combined organic extracts were washed with H2O (1 x 100 mL), brine (1 x 100 mL), dried (Na2SO4) and concentrated under reduced pressure to give a solid. Purification by flash chromatography, elution with 20% EtOAc-hexane, to provide 1.19 g (59%) of the 4-nitro-trifluoracetanilide compound as a yellow solid. A mixture of the nitro compound prepared as above (1.14 g, 3.36 mmol), MeOH (33 mL), and H2O (13mL) was treated with K2CO3 (2.32 g, 16.8 mmol) and heated at reflux for 2h. The reaction mixture was cooled to room temperature and MeOH was removed under reduced pressure. The aqueous residue was extracted with EtOAc (2 x 200 mL). The combined organic extracts were washed with H2O (1 x 100 mL), brine (1 x 100 mL), dried (Na2SO4) and concentrated under reduced pressure to give Int-4, in quantitative yield, as a yellow solid.
  • 85
  • hexane-washed NaH [ No CAS ]
  • [ 5292-43-3 ]
  • [ 404-24-0 ]
  • [ 65171-67-7 ]
YieldReaction ConditionsOperation in experiment
93% With sodium hydroxide; aniline; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; (b) t-Butyl N-Phenylglycinate (IV). A solution consisting of 15 g of trifluoroacetanilide (previously prepared by the reaction of trifluoroacetic anhydride with aniline in ethyl ether at about 0 over a 30 min period) in 20 mL dry THF was added dropwise to a stirred suspension of hexane-washed NaH (4.19 g) in 100 mL THF at room temperature over a 1 hr period. The mixture was stirred for an additional 30 min following which t-butyl bromoacetate (16.2 g; 0.83 mole) was added to this reaction mixture. After further stirring for 16 hr, the reaction mixture was concentrated in vacuo to a residue which was then suspended in 200 mL ether and filtered using Celite or a comparable filter aid. The filtrate was concentrated in vacuo to a residual oil which was dried under high vacuum (0.02 mm Hg) for 16 hr to yield, in essentially quantitative yield, 24.1 g of an orange oil, t-butyl N-phenyl-N-trifluoroacetylglycinate. This oily intermediate was combined with 150 mL 1N NaOH solution in 150 mL THF and heated at 50 C. for 90 min. The THF was removed in vacuo and the resulting aqueous oil mixture was extracted with three 150 mL portions of CHCl3. These CHCl3 extracts were combined, dried (MgSO4) and concentrated to a residue which was chromatographed on silica gel eluding with hexane-EtOAC (19:1) to give 15.2 g (93% yield) of product in the form of a pale yellow oil which can be used without purification in reaction (c).
  • 86
  • [ 404-24-0 ]
  • N-(1-MethylethylN-[3-(1-methylethylamino]propyl4[(trifluoroacetyl)amino]benzenesulfonamide, hydrochloride [ No CAS ]
  • [ 31143-71-2 ]
YieldReaction ConditionsOperation in experiment
With chlorosulfonic acid; EXAMPLE 3 N-(1-methylethylN-[3-(1-methylethylamino]propyl4[(trifluoroacetyl)amino]benzenesulfonamide, hydrochloride, 2/3 isopropanol Chlorosulfonic acid (100 g.) was cooled to 0 C. and trifluoroacetanilide (30 g.) was added portionwise with vigorous stirring keeping the temperature below +5 C. The reaction was stirred at room temperature overnight, and cautiously poured onto ice. The white solid produced was filtered, washed copiously with water, and dried to give 4-trifluoroacetamido benzenesulfonyl chloride (39.14 gl)(m.r. 143-146 C.). Analysis for: C8 H5 ClF3 O3 NS, Calculated: C, 33.41; H, 1.75; N, 4.87, Found: C, 33,34; H, 1.65; N, 4.82.
  • 88
  • [ 404-24-0 ]
  • [ 75-24-1 ]
  • [ 439930-56-0 ]
  • 89
  • [ 404-24-0 ]
  • [ 31143-71-2 ]
YieldReaction ConditionsOperation in experiment
With chlorosulfonic acid; at 155℃; for 0.25h; A mixture of acetamide (1 equivalent) and chlorosulfonic acid (5 equivalent) was heated at 155 C. for 15 min. After cooling to RT, the mixture was poured into ice water and extracted with EtOAc. The organic layer was concentrated and purified via silica gel chromatography using 7/3 hexanes/EtOAc gave desired product.
  • 90
  • [ 931-53-3 ]
  • [ 404-24-0 ]
  • [ 762-42-5 ]
  • [ 1185254-50-5 ]
  • 91
  • [ 404-24-0 ]
  • [ 79-03-8 ]
  • [ 620-71-3 ]
  • 92
  • [ 404-24-0 ]
  • [ 3282-30-2 ]
  • [ 6625-74-7 ]
  • 93
  • [ 404-24-0 ]
  • [ 75-36-5 ]
  • [ 103-84-4 ]
  • 94
  • [ 61881-11-6 ]
  • [ 404-24-0 ]
  • 95
  • [ 98-95-3 ]
  • [ 76-05-1 ]
  • [ 404-24-0 ]
  • 96
  • [ 404-24-0 ]
  • [ 64-19-7 ]
  • [ 959710-84-0 ]
  • 97
  • [ 404-24-0 ]
  • [ 1228757-61-6 ]
  • N-phenyl-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl) trifluoroacetimidate [ No CAS ]
  • 98
  • [ 62-53-3 ]
  • [ 183266-61-7 ]
  • [ 404-24-0 ]
  • 99
  • [ 404-24-0 ]
  • [ 104-15-4 ]
  • [ 1323117-30-1 ]
YieldReaction ConditionsOperation in experiment
44% With [hydroxy(tosyloxy)iodo]benzene; boron trifluoride diethyl etherate; In acetonitrile; at 20℃; for 0.5h; General procedure: To a stirred solution of anilide 1a (1a-1m, 0.2 mmol) and BF3·OEt2 (0.038 mL, 0.3 mmol) in acetonitrile (1.0 mL) at room temperature, was added PIFA (0.129g, 0.3 mmol) and arylsulfonic acid (0.6 mmol). The resulting mixture was stirred at room temperature for 0.5 h. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography using petroleum ether/EtOAc as the eluent to afford pure product 2a (2b-2o)
  • 100
  • [ 1228956-85-1 ]
  • [ 407-25-0 ]
  • [ 404-24-0 ]
  • 101
  • [ 914264-19-0 ]
  • [ 407-25-0 ]
  • [ 404-24-0 ]
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