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Structure of 327-74-2 * Storage: {[proInfo.prStorage]}
* 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.
With potassium carbonate; nickel(II) hydroxide In dimethyl sulfoxide at 35℃; for 2 h;
The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is p-cyanoaniline, the reaction time is 12 h, and the other reaction and post-treatment processes are the same as in the embodiment 28. The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is aniline, and the nickel compound is nickel hydroxide.The base is potassium carbonate, and the reaction process parameters are: 1-trifluoromethyl-1,2-phenyliodo-3(H)-one (0.5 mmol, 1.0 eq).Aromatic amine (1.5 mmol, 3.0 eq), nickel hydroxide 10 molpercent, potassium carbonate (1.5 mmol, 3.0 eq),DMSO (2 mL) was reacted at 35 ° C for 2 h, and the other reactions and workup procedures were the same as in Example 1.
Reference：
[1] Organic Letters, 2018, vol. 20, # 13, p. 3732 - 3735
[2] Patent: CN108503552, 2018, A, . Location in patent: Paragraph 0126-0130
[3] Organic Letters, 2014, vol. 16, # 6, p. 1768 - 1771
2
[ 557-21-1 ]
[ 97760-97-9 ]
[ 327-74-2 ]
Yield
Reaction Conditions
Operation in experiment
99.28%
for 12 h;
Step 2: 4-Amino-3-trifluoromethylbenzonitrile4-lodo-2-trifluoromethylphenylamine (50mg, 0.17mmol), Zn(CN)2 (O.δδeq, 0.15mmol, 18.00mg), and Pd(PPh3)4(0.1eq, 0.02mmol, 19.64mg) were added in DMF. Zn(CN)2(0.88eq, 0.15mmol, 18.00mg) and Pd(PPh3)4(0.1eq, 0.02mmol, 19.64mg) were added into the reaction mixture. The reaction mixture was stirred for 12hr. The reaction mixture was purified according to step 1 of Example 8 to give a title product as a yellow solid (31.4mg, 99.28percent).Mp: 54-56 °C ; IR( KBr pellet, crrf1): 3385, 3263, 2924, 2220, 1124, 7011H NMR (400MHz, CDCl3): δ 7.65(d, 1 H, J =2.0Hz), 7.45(dd, 1 H, J =8.4, 2.0Hz), 6.69(d,1H, J =8.4Hz), 4.65(s, 2H)
99.28%
for 12 h;
4-lodo-2-trifluoromethylphenylamine (50mg, 0.17mmol), Zn(CN)2 (0.88eq, 0.15mmol, 18.00mg), and Pd(PPh3)4(0.1eq, 0.02mmol, 19.64mg) were added DMF. Zn(CN)2 (0.88eq, 0.15mmol, 18.00mg) and Pd(PPh3)4(0.1eq, 0.02mmol, 19.64mg) were added into the reaction mixture. The reaction mixture was stirred for 12hrs. The reaction mixture was purified according to step 1 of Example 8 to give the title product, as a yellow solid (31.4 mg, 99.28percent). mp: 54-56 °C; IR (KBr pellet, cm-1): 3385, 3263, 2924, 2220, 1124, 701 1H NMR (400MHz, CDCl3): δ 7.65(d, 1 H, J=2.0Hz), 7.45(dd, 1 H, J =8.4, 2.0Hz), 6.69(d, 1 H, J =8.4Hz), 4.65(s, 2H).
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); potassium carbonate In 1,2-dichloro-ethane at 20℃; for 24 h; Inert atmosphere; Schlenk technique; Irradiation
General procedure: A 25 mL of Schlenk tube equipped with a magnetic stir bar were charged with aniline (1.2 mmol, 3.0 equiv) or heterocycles (0.8 mmol, 2.0 equiv), K2CO3 (0.8 mmol, 2.0 equiv) and fac-Ir(ppy)3 (2.6 mg, 0.004 mmol, 1 mol percent), under air. The vessel was evacuated and backfilled with Ar (3 times), CF3I stock solution (0.56 mL, 0.71 mmol/mL in 1,2-chloroethane or 0.36 mL, 1.11 mmol/mL in DMSO, 1.0 equiv), anhydrous 1,2-dichloroethane (3 mL) were then added. The tube was screw capped and stirred at room temperature under irradiation of blue LEDs (12 W) for 24 hours. The reaction S15 mixture was filtered through a pad of Celite and washed with ethyl acetate (3×5 mL). The filtrate was concentrated. The residue was subjected to column chromatography on silica gel to afford the pure product.
Reference：
[1] Chemical Communications, 2012, vol. 48, # 62, p. 7756 - 7758
9
[ 67-56-1 ]
[ 327-74-2 ]
[ 167760-75-0 ]
Yield
Reaction Conditions
Operation in experiment
76%
at 0℃; for 6.2 h; Heating / reflux
81.70 g (439 mmol) 4-amino-3-trifluoromethyl-benzonitrile are dissolved in 1000 ml of methanol, cooled to 0° C. Within 1.2 hours hydrochloric acid is added in gaseous form. Then the reaction mixture is refluxed for 5 hours with stirring, then diluted with water, cooled to 3° C. and suction filtered. The precipitate is washed with water and dried. Yield: 73.10 g (76percent of theoretical)
1-phenyl-5-(4-cyano-2-trifluoromethylanilino)tetrazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate;
SYNTHESIS EXAMPLE 1 STR16 4-Amino-3-trifluoromethyl-benzonitrile (0.9 g) was added to a tetrahydrofuran solution (25 ml) of sodium hydride (0.5 g; 60% in oil) at room temperature. The mixture was stirred at room temperature for about 10 minutes until the generation of hydrogen gas was ceased. Then, 5-chloro-1-phenyltetrazole (0.9 g) was added thereto and the mixture was stirred for 2 hours. The reaction solution was poured into 100 ml of ice water and the organic layer was distilled off under reduced pressure. Activated carbon was added to the aqueous layer and the aqueous layer was filtered. Then, the pH of the filtrate was adjusted to 2-3 with concentrated hydrochloric acid. The precipitated crystals were collated by filtration and washed with water and n-hexane to obtain 1-phenyl-5-(4-cyano-2-trifluoromethylanilino)tetrazole (1.5 g). melting point: 154-156 C.
tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; for 12h;
Step 2: 4-Amino-3-trifluoromethylbenzonitrile4-lodo-2-trifluoromethylphenylamine (50mg, 0.17mmol), Zn(CN)2 (O.deltadeltaeq, 0.15mmol, 18.00mg), and Pd(PPh3)4(0.1eq, 0.02mmol, 19.64mg) were added in DMF. Zn(CN)2(0.88eq, 0.15mmol, 18.00mg) and Pd(PPh3)4(0.1eq, 0.02mmol, 19.64mg) were added into the reaction mixture. The reaction mixture was stirred for 12hr. The reaction mixture was purified according to step 1 of Example 8 to give a title product as a yellow solid (31.4mg, 99.28%).Mp: 54-56 C ; IR( KBr pellet, crrf1): 3385, 3263, 2924, 2220, 1124, 7011H NMR (400MHz, CDCl3): delta 7.65(d, 1 H, J =2.0Hz), 7.45(dd, 1 H, J =8.4, 2.0Hz), 6.69(d,1H, J =8.4Hz), 4.65(s, 2H)
99.28%
tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; for 12h;
4-lodo-2-trifluoromethylphenylamine (50mg, 0.17mmol), Zn(CN)2 (0.88eq, 0.15mmol, 18.00mg), and Pd(PPh3)4(0.1eq, 0.02mmol, 19.64mg) were added DMF. Zn(CN)2 (0.88eq, 0.15mmol, 18.00mg) and Pd(PPh3)4(0.1eq, 0.02mmol, 19.64mg) were added into the reaction mixture. The reaction mixture was stirred for 12hrs. The reaction mixture was purified according to step 1 of Example 8 to give the title product, as a yellow solid (31.4 mg, 99.28%). mp: 54-56 C; IR (KBr pellet, cm-1): 3385, 3263, 2924, 2220, 1124, 701 1H NMR (400MHz, CDCl3): delta 7.65(d, 1 H, J=2.0Hz), 7.45(dd, 1 H, J =8.4, 2.0Hz), 6.69(d, 1 H, J =8.4Hz), 4.65(s, 2H).
With Iodine monochloride; In dichloromethane; for 12h;
Step 3: 4-Amino-3-iodo-5-trifluoromethylbenzonitrile4-Amino-3-trifluoromethylbenzonitrile (100mg, 0.54mmol) and ICI(1.1eq, 0.58mmol, 96.00mg) were added methylene chloride. The mixture was stirred for 12hr. The reaction mixture was purified accoding to step 2 of Example 8 to give a title compound (30.5mg, 18.10%).mp: 86-880C;IR (KBr pellet, cm"1): 3371 , 3080, 2924, 2226, 1125, 701 ; 1H NMR (400MHz, CDCI3): delta 8.02 (d, 1 H, J=1.6Hz), 7.35 (dd, 1 H, J=133.2, 1.6Hz), 7.65 (dd, 1 H, J=10.0, 1.6Hz), 5.20 (d, 2H, J=22.0Hz).
18.10%
With Iodine monochloride; In dichloromethane; for 12h;
4-Amino-3-trifluoromethylbenzonitrile (100mg, 0.54mmol) and lCl(1.1eq, 0.58mmol, 96.00mg) were added to methylene chloride. The mixture was stirred for 12hrs. The reaction mixture was purified accoding to step 2 of Example 8 to give the title compound (30.5mg, 18.10%). mp: 86~88 C; IR(KBr pellet, cm-1): 3371, 3080, 2924, 2226, 1125, 701; 1H NMR(400MHz, CDCl3): delta 8.02 (d, 1 H, J=1.6Hz), 7.35 (dd, 1 H, J=133.2, 1.6Hz), 7.65 (dd, 1H, J=10.0, 1.6Hz), 5.20 (d, 2H, J=22.0Hz).
With n-Amyl nitrite; at 50℃; for 3h;Heating / reflux;Product distribution / selectivity;
a) 2-Trifluoromethyl-biphenyl-4-carbaldehyde oximeStep a) To a solution of 4-cyano-2-trifluoroaniline (1 eq) in benzene there is added under inert atmosphere n-pentylnitrite (1 eq) at 5O0C. After one hour refluxing a second equivalent of n-pentylnitrite is added. After additional two hours of refluxing the reaction mixture is cooled to room temperature and concentrated under reduced pressure. The dark residue is purified on silica gel using c-hexane-> c-hexane/ethyl acetate 9/1 as mobile phase (pale orange oil).; Step a) To a solution of 4-cyano-2-trifluoroaniline (1 eq) in benzene there is added under inert atmosphere n-pentylnitrite (1 eq) at 5O0C. After one hour refluxing a second equivalent of n-pentylnitrite is added. After additional two hours of refluxing the reaction mixture is cooled to room temperature and concentrated under reduced pressure. The dark residue is purified on silica gel using c-hexane-> c-hexane/ethyl acetate 9/1 as mobile phase (pale orange oil).
With hydrogenchloride; at 0℃; for 6.2h;Heating / reflux;
81.70 g (439 mmol) 4-amino-3-trifluoromethyl-benzonitrile are dissolved in 1000 ml of methanol, cooled to 0 C. Within 1.2 hours hydrochloric acid is added in gaseous form. Then the reaction mixture is refluxed for 5 hours with stirring, then diluted with water, cooled to 3 C. and suction filtered. The precipitate is washed with water and dried. Yield: 73.10 g (76% of theoretical)
With Ki; sodium thiosulfate; sodium nitrite; In HBF4; water; acetone; toluene;
Intermediate I-IX-6 (I-19): 4-iodo-3-(trifluoromethyl)benzonitrile To a slurry of <strong>[327-74-2]4-amino-3-(trifluoromethyl)benzonitrile</strong> (5.48 g; 29.5 mmol) in HBF4 (50 mL; 48%) at -10 C. was added NaNO2 (2.24 g; 32.4 mmol), portionwise over 10 min. The mixture was stirred 30 min, precipitated solids were collected by filtration (Note 1) and (without delay) added portionwise to a solution of KI (7.84 g; 47.2 mmol) in acetone/water (50 mL of a 40% v/v solution). The mixture was decolorized by addition of 10 wt % Na2S2O3, precipitate was collected by filtration, washed with water and slurried in PhMe. The slurry was concentrated to dryness, affording the title compound as a pale orange solid, used without further purification. 1H NMR (400 MHz, DMSO-d6) delta 7.83 (dd, J=8.1, 1.6 Hz, 1H), 8.27 (d, J=1.5 Hz, 1H), 8.37 (d, J=8.1 Hz, 1H).
With Ki; sodium thiosulfate; sodium nitrite; In HBF4; water; acetone; toluene;
Intermediate I-IX-6 (I-19): 4-iodo-3-(trifluoromethyl)benzonitrile To a slurry of <strong>[327-74-2]4-amino-3-(trifluoromethyl)benzonitrile</strong> (5.48 g; 29.5 mmol) in HBF4 (50 mL; 48%) at -10 C. was added NaNO2 (2.24 g; 32.4 mmol), portionwise over 10 min. The mixture was stirred 30 min, precipitated solids were collected by filtration (Note 1) and (without delay) added portionwise to a solution of KI (7.84 g; 47.2 mmol) in acetone/water (50 mL of a 40% v/v solution). The mixture was decolorized by addition of 10 wt % Na2S2O3, precipitate was collected by filtration, washed with water and slurried in PhMe. The slurry was concentrated to dryness, affording the title compound as a pale orange solid, used without further purification. 1H NMR (400 MHz, DMSO-d6) delta 7.83 (dd, J=8.1, 1.6 Hz, 1H), 8.27 (d, J=1.5 Hz, 1H), 8.37 (d, J=8.1 Hz, 1H). Note 1 Solid was not allowed to dry completely on the filter.
To a slurry of <strong>[327-74-2]4-amino-3-(trifluoromethyl)benzonitrile</strong> (5.48 g; 29.5 mmol) in HBF4(50 mL; 48%) at -10 C. was added NaNO2(2.24 g; 32.4 mmol), portionwise over 10 min. The mixture was stirred 30 min, precipitated solids were collected by filtration (Note 1) and (without delay) added portionwise to a solution of KI (7.84 g; 47.2 mmol) in acetone/water (50 mL of a 40% v/v solution). The mixture was decolorized by addition of 10 wt % Na2S2O3, precipitate was collected by filtration, washed with water and slurried in PhMe. The slurry was concentrated to dryness, affording the title compound as a pale orange solid, used without further purification.
With sodium hydride; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;
To a solution of <strong>[327-74-2]2-amino-5-cyanobenzotrifluoride</strong> (1.0g, 5.37mmol, 1 eq) and benzyl bromide (2.55ml_, 21 .5mmol, 4.0eq) in dry DMF (10ml_) was added at rt NaH (970mg, 21.5mmol, 4eq) portion-wise under Ar(g). The reaction mixture was stirred at rt overnight, and was then partitioned with H20 (30ml_) and extracted with EtOAc (5 x 20ml_) and CH2CI2 (20ml_). The combined organic extracts were dried over MgS04 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (1 :0-9:1 ) to yield the product, 2, as a pale yellow solid (1 .66g, 85%).1H NMR (400MHz, CDCI3) deltaEta: 7.95 (d, J=2.0Hz, 1 H), 7.63 (dd, J=8.5, 1 .5Hz, 2H), 7.28-7.34 (m, 6H), 7.20 (d, J=6.5Hz, 4H), 7.12 (d, J=8.5Hz, 1 H), 4.23 (s, 4H).MS (ES+) 389.1 (100%, [M+Na]+).
85%
With sodium hydride; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;
i. 4-Dibenzylamino-3-trifluoromethyl-benzonitrile, 2 To a solution of <strong>[327-74-2]2-amino-5-cyanobenzotrifluoride</strong> (1.0 g, 5.37 mmol, 1 eq) and benzyl bromide (2.55 mL, 21.5 mmol, 4.0 eq) in dry DMF (10 mL) was added at rt NaH (970 mg, 21.5 mmol, 4 eq) portion-wise under Ar (g). The reaction mixture was stirred at rt overnight, and was then partitioned with H2O (30 mL) and extracted with EtOAc (5*20 mL) and CH2Cl2 (20 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (1:0-9:1) to yield the product, 2, as a pale yellow solid (1.66 g, 85%). 1H NMR (400 MHz, CDCl3) deltaH: 7.95 (d, J=2.0 Hz, 1H), 7.63 (dd, J=8.5, 1.5 Hz, 2H), 7.28-7.34 (m, 6H), 7.20 (d, J=6.5 Hz, 4H), 7.12 (d, J=8.5 Hz, 1H), 4.23 (s, 4H). MS (ES+) 389.1 (100%, [M+Na]+).
With triethylamine; In dichloromethane; at 20℃;Reflux;
General procedure: The compound 1(4-(chloromethyl)benzoyl chloride, 12 mmol) was added dropwise to a mixture of 2a-n (10 mmol) and triethylamine (12 mmol) in dichloromethane (20 mL) at room temperature with stirring. Then the reaction mixture was refluxed for 4-6 h. After cooling to room temperature, the mixture was slowly poured to ice water (50 mL). The solution was extracted with dichloromethane (3×60 mL) and the organic phase was dried over with sodium sulfate anhydrous. After removal of the dichloromethane, the solid residue was purified by recrystallization with petroleum ether-ethyl acetate to give compounds 3a-n.
With potassium carbonate; In acetonitrile; at 75℃; for 6h;Schlenk technique; Inert atmosphere;
General procedure: Experimental Procedure: A dried 25 mL Schlenk tube equipped with a magnetic stir bar was charged with Togni?s Reagent 2 (0.25 mmol, 1.0 equiv), free anilines 1 (0.75 mmol, 3.0 equiv), K2CO3 (0.375 mmol, 1.5 equiv) and CH3CN (1.5 mL). The reaction mixture was then stirred at 75 C for 6 h under an argon atmosphere. The reaction progress was monitored by TLC. After cooling to room temperature, the mixture was washed with water and extracted with CH2Cl2 three times, then washed with saturated NaCl solution. The combined organic layer was dried with anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel (Elutent: petroleum ether-EtOAc) to give the pure product. The products were characterized by 1H NMR, 13C NMR, 19F NMR, GC -MS.
67%
With potassium carbonate; nickel(II) hydroxide; In dimethyl sulfoxide; at 35℃; for 2h;
The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is p-cyanoaniline, the reaction time is 12 h, and the other reaction and post-treatment processes are the same as in the embodiment 28. The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is aniline, and the nickel compound is nickel hydroxide.The base is potassium carbonate, and the reaction process parameters are: 1-trifluoromethyl-1,2-phenyliodo-3(H)-one (0.5 mmol, 1.0 eq).Aromatic amine (1.5 mmol, 3.0 eq), nickel hydroxide 10 mol%, potassium carbonate (1.5 mmol, 3.0 eq),DMSO (2 mL) was reacted at 35 C for 2 h, and the other reactions and workup procedures were the same as in Example 1.
N-(4-cyano-2-(trifluoromethyl)phenyl)methacrylamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
95%
In N,N-dimethyl acetamide; at 20℃; for 3h;Inert atmosphere;
General procedure: Methacryloyl chloride 6 (2.63 mL, 27.16 mmol) was added over the course of 10 minutes to a stirring solution of the different aniline 7-11 (3.4 mmol) in N,N- dimethylacetamide (14 mL) at r.t. for 3 h or o.n. After the reaction was complete, the mixture was diluted with ethyl acetate (100 mL), extracted with sat. aq. NaHCO3 solution (3x25 mL) and with cold brine (4x50 mL). The organic layer was dried over Na2SO4 and the solvent vas removed at reduced pressure. The crude residue was purified by flash column chromatography.
95%
In N,N-dimethyl acetamide; at 20℃; for 3h;Inert atmosphere;
General procedure: Methacryloyl chloride 5 (2.63 mL, 27.16 mmol) was added overthe course of 10 min to a stirring solution of the different aniline6e14 (3.4 mmol) in N,N-dimethylacetamide (14 mL) at r.t. for 3 h oro.n. After the reaction was complete, the mixture was diluted withethyl acetate (100 mL), extracted with sat. aq. NaHCO3 solution(3 25 mL) and with cold brine (4 50 mL). The organic layer wasdried over Na2SO4 and the solvent vas removed at reduced pressure.The crude residue was purified by flash columnchromatography.
88%
In N,N-dimethyl acetamide; at 20℃;
General procedure: Methacryloyl chloride 5 (8.4 mL, 85.96 mmol) was added overthe course of 10 min to a stirring solution of the appropriatetrifluoromethyl-substituted aniline 1e4 (10.75 mmol) in N, N-dimethylacetamide (10 mL) at room temperature for 24 h. After thereaction was complete, the mixture was diluted with ethyl acetate(100 mL), extracted with saturated NaHCO3 solution (2 x 50 mL)then cold brine (2 x 50 mL). The combined organic layer was driedover anhydrous Na2SO4 and the solvent was removed underreduced pressure. The crude oil residue was purified by flash columnchromatography eluting with chloroform-ethyl acetate 95:5 v/v to obtain the titled compounds.
In N,N-dimethyl acetamide; at 20℃; for 1.66667h;Inert atmosphere;
General procedure: Methacryloylchloride 5 (2.63 mL, 27.16 mmol) wasadded over the course of 10 minutes to a stirring solution of the differentaniline 6-11 (3.4 mmol) inN,N-dimethylacetamide (14 mL) at r.t. for 3 h or o.n. After the reaction wascomplete, the mixture was diluted with ethyl acetate (100 mL), extracted withsat. aq. NaHCO3 solution (3x25 mL) and with cold brine (4x50 mL).The organic layer was dried over Na2SO4 and the solventvas removed at reduced pressure. The crude residue was purified by flash columnchromatography
4-isothiocyanato-3-(trifluoromethyl)benzonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
99%
With sodium hydrogencarbonate; In water; toluene; at 0 - 75℃; for 120h;Inert atmosphere;
General procedure: A solution of NaHCO3 (0.82 g) in distilled water (4 mL) was stirred for 10 minutes and to it was added DCM (4 mL) followed by the different aniline 7-10, 53 (2.4mmol). The reaction mixture was cooled to 0 C, thiophosgene (0.3 mL, 3.7 mmol) was added dropwise over 10 minutes and the reaction was then stirred at r.t. o.n. The mixture was then diluted with DCM (20 mL), washed with brine (20 mL), the organic layer was dried over Na2SO4 and concentrated to dryness. Aniline 9 (4.9 mmol) was dissolved in 9 mL toluene. Thiophosgene (10.67 mmol) was added dropwise and the mixture was stirred at 75 C for five days. Obtained in99% yield as a brown wax
75%
With sodium hydrogencarbonate; In dichloromethane; water; at 0 - 20℃;Inert atmosphere;
General procedure: A solution of NaHCO3 (0.82 g) in distilled water (4 mL) wasstirred for 10 min and to it was added DCM (4 mL) followed by thedifferent aniline 7e12 (2.4 mmol). The reaction mixture was cooledto 0 C, thiophosgene (0.3 mL, 3.7 mmol) was added dropwise over10 min and the reaction was then stirred at r.t. overnight. Themixture was then diluted with DCM (20 mL), washed with brine(20 mL), the organic layer was dried over Na2SO4 and concentratedto dryness.
In dichloromethane; water; at 0 - 20℃; for 24h;Inert atmosphere;
General procedure: A solution of NaHCO3 (0.82 g) in distilledwater (4 mL) was stirred for 10 minutes and to it was added DCM (4 mL) followedby the different aniline 6-9, 11(2.4 mmol). The reaction mixture was cooled to 0 C, thiophosgene (0.3 mL, 3.7mmol) was added dropwise over 10 minutes and the reaction was then stirred atr.t. o.n. The mixture was then diluted with DCM (20 mL), washed with brine (20mL), the organic layer was dried over Na2SO4 andconcentrated to dryness.
(R)-(-)-3-bromo-4’-cyano-2-hydroxy-2-methyl-2’-(trifluoromethyl)propionanilide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In N,N-dimethyl acetamide; at 20℃;Inert atmosphere;
General procedure: Thionyl chloride (4.3 g, 36 mmol) was added dropwise under argon to a solution of bromoacid 39 (5.5 g, 30 mmol) in 35 mL of DMA at -5 to -10 C. The resulting mixture was stirred for 2 h under the same conditions. A solution of the appropriate aniline (30 mmol) in 40 mL of DMA was added dropwise to the above solution, and the resulting mixture was stirred overnight at room temperature. The solvent was removed on rotavapor using high vacuum oil pump; the residue was diluted with saturated NaHCO3 solution, and extracted with ethyl ether (3 x 100 mL). Combined extracts were dried over anhydrous Na2SO4, filtered through celite, and purified by flash chromatography on silica gel, using DCM as eluent to afford the desired product.
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