No renderable structure data available
FC(C(NC1C=CC=CC=1)=O)(F)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | .alpha.,.alpha.-Trifluoroacetanilide |
|---|---|
| IUPAC Name | — |
| CAS Number | 404-24-0 |
| Database ID | 67881 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
.alpha.,.alpha.-Trifluoroacetanilide (CAS 404-24-0) 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 67881
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-6605ace53b7e4a7282b33b8155aa1ae0Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d0b750179e254cb388baeaa26f336e2bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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.). the temperature below +5° C The reaction was stirred at room temperature overnight cautiously poured onto ice The white solid produced was filtered washed copiously with water dried
Source ID: ord-ed5937b650f7415296cb11e2862453deConditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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 HCl (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. The resulting reaction mixture The reaction mixture is then evaporated under reduced pressure This aqueous mixture is extracted with ethyl acetate (3×15 mL) dried (MgSO4) evaporated under reduced pressure chromatographed silica gel (approximately 50 g) and elution with an appropriate solvent system
Source ID: ord-95527d8d85d44eebb228c2f45fc656ddConditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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 HCl (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. The resulting reaction mixture The reaction mixture is then evaporated under reduced pressure This aqueous mixture is extracted with ethyl acetate (3×15 mL) dried (MgSO4) evaporated under reduced pressure chromatographed silica gel (approximately 50 g) and elution with an appropriate solvent system
Source ID: ord-54c7d2970c01459db69074daf15ff12eConditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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 HCl (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. The resulting reaction mixture The reaction mixture is then evaporated under reduced pressure This aqueous mixture is extracted with ethyl acetate (3×15 mL) dried (MgSO4) evaporated under reduced pressure chromatographed silica gel (approximately 50 g) and elution with an appropriate solvent system
Source ID: ord-54c7d2970c01459db69074daf15ff12eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(Cyclopropylmethyl)aniline [NMR (200 MHz, DMSO-d6): δ0.21 (m, 2H); 0.51 (m, 2H); 1.01 (m, 1H); 3.63 (d, J=7.3 Hz, 1H); 3.80 (br s, 1H); 5.78 (br s, 1H); 7.18 (t, J=7.2 Hz, 1H); 7.25 (d, J=7.8 Hz, 2H); 7.42 (t, J=7.3 Hz, 2H)] was prepared from aniline and (bromomethyl)cyclopropane via trifluoroacetanilide using the general method described by Hodge (Harland, P. A.; Hodge, P; Maughan, W.; Wildsmith, E. Synthesis, 1984, 941.). Synthesis, 1984, 941
Source ID: ord-08f7366b5793408aa2dfa517fd7859c1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(Cyclopropylmethyl)aniline [NMR (200 MHz, DMSO-d6): δ0.21 (m, 2H); 0.51 (m, 2H); 1.01 (m, 1H); 3.63 (d, J=7.3 Hz, 1H); 3.80 (br s, 1H); 5.78 (br s, 1H); 7.18 (t, J=7.2 Hz, 1H); 7.25 (d, J=7.8 Hz, 2H); 7.42 (t, J=7.3 Hz, 2H)] was prepared from aniline and (bromomethyl)cyclopropane via trifluoroacetanilide using the general method described by Hodge (Harland, P. A.; Hodge, P; Maughan, W.; Wildsmith, E. Synthesis, 1984, 941.). Synthesis, 1984, 941
Source ID: ord-08f7366b5793408aa2dfa517fd7859c1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-Allylaniline [NMR (200 MHz, DMSO-d6): δ3.68 (t, J=5.2 Hz, 2H); 5.10 (d, J=10.2 Hz, 1H); 5.23 (d, J=17.2 Hz, 1H); 5.78 (br s, 1H); 5.75-5.97 (m, 1H); 6.52 (t, J=7.3 Hz, 2H); 6.56 (d, J=7.8 Hz, 2H); 7.06 (t, J=7.3 Hz, 2H)] was prepared from aniline and allyl bromide via trifluoroacetanilide using the general method described by Hodge (Harland, P.A.; Hodge, P; Maughan, W.; Wildsmith, E. Synthesis, 1984, 941). described by Hodge (Harland, P.A.; Hodge, P; Maughan, W.; Wildsmith, E. Synthesis, 1984, 941)
Source ID: ord-627ef3d791574c29a32f02e4e0e88ebbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of (R)-5-amino-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (28.7 g, 75.2 mmol, described in Intermediate 3) in CH2 Cl2 (100 mL) was added trifluoroacetic anhydride (106 mL, 752 mmol). The mixture was stirred for 10 min, after which time the aniline had been converted to the corresponding trifluoroacetanilide. The resulting mixture was cooled in an ice-salt bath and 15.8 M nitric acid (5.0 mL, 79 mmol) was added dropwise over 15 min, keeping the reaction temperature at 10-12° C. After the addition, the reaction mixture was stirred for 30 min, then H2O (12 mL) was carefully added, followed by trifluoroacetic acid (100 mL) and CH2 Cl2 (100 mL). The mixture was allowed to warm to ambient temperature and stirring was continued for 2 h, followed by concentration to dryness in vacuo. The residue was dissolved in MeOH (200 mL) and the solution was adjusted to pH 10 by addition of 10 N NaOH. Ethylene diamine (5 mL, 75 mmol) was added and the mixture was stirred at ambient temperature for 18 h, then diluted with H2O (200 mL). The resulting solid was isolated by filtration, washed with H2O, and dried in vacuo to give the title compound. MS: m/z=297 (M+1). The resulting mixture was cooled in an ice-salt bath at 10-12° C After the addition the reaction mixture was stirred for 30 min stirring was continued for 2 h followed by concentration to dryness in vacuo The residue was dissolved in MeOH (200 mL) the solution was adjusted to pH 10 by addition of 10 N NaOH the mixture was stirred at ambient temperature for 18 h The resulting solid was isolated by filtration washed with H2O dried in vacuo
Source ID: ord-869ef5b5c94d4b77ae0150ff681573d5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of (R)-5-amino-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (28.7 g, 75.2 mmol, described in Intermediate 3) in CH2 Cl2 (100 mL) was added trifluoroacetic anhydride (106 mL, 752 mmol). The mixture was stirred for 10 min, after which time the aniline had been converted to the corresponding trifluoroacetanilide. The resulting mixture was cooled in an ice-salt bath and 15.8 M nitric acid (5.0 mL, 79 mmol) was added dropwise over 15 min, keeping the reaction temperature at 10-12° C. After the addition, the reaction mixture was stirred for 30 min, then H2O (12 mL) was carefully added, followed by trifluoroacetic acid (100 mL) and CH2 Cl2 (100 mL). The mixture was allowed to warm to ambient temperature and stirring was continued for 2 h, followed by concentration to dryness in vacuo. The residue was dissolved in MeOH (200 mL) and the solution was adjusted to pH 10 by addition of 10 N NaOH. Ethylene diamine (5 mL, 75 mmol) was added and the mixture was stirred at ambient temperature for 18 h, then diluted with H2O (200 mL). The resulting solid was isolated by filtration, washed with H2O, and dried in vacuo to give the title compound. MS: m/z=297 (M+1). The resulting mixture was cooled in an ice-salt bath at 10-12° C After the addition the reaction mixture was stirred for 30 min stirring was continued for 2 h followed by concentration to dryness in vacuo The residue was dissolved in MeOH (200 mL) the solution was adjusted to pH 10 by addition of 10 N NaOH the mixture was stirred at ambient temperature for 18 h The resulting solid was isolated by filtration washed with H2O dried in vacuo
Source ID: ord-869ef5b5c94d4b77ae0150ff681573d5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2,2,2-trifluoro-N-phenylacetamide (5.0 g, 26 mmol) in THF (10 mL) was added BH3 in THF (130 mL, 130 mmol, 1.0 M). The resulting mixture was refluxed overnight. The mixture was quenched with water and methanol, concentrated to remove most of THF, and extracted with EtOAc. Organics were washed with brine, dried (Na2SO4), and concentrated to give 4.17 g (92%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.71-3.75 (2H, m), 6.66 (2H, d, J=8.0 Hz), 6.79 (1H, t, J=7.2 Hz), 7.20 (2H, t, J=8.0 Hz). The resulting mixture was refluxed overnight The mixture was quenched with water and methanol concentrated to remove most of THF extracted with EtOAc Organics were washed with brine dried (Na2SO4) concentrated
Source ID: ord-9dd051ce3196484590c650f2598c4c36PubChem References
These sources are listed in the compound's public database record.
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