1184936-21-7|4-Chloro-2-(trifluoroacetyl)aniline Hydrochloride Hydrate| Ambeed

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Quality Control of [ 1184936-21-7 ] Purity: 98% SDS Specification

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Product Details of [ 1184936-21-7 ]

CAS No. :	1184936-21-7
Formula :	C₈H₈Cl₂F₃NO₂
M.W :	278.06
SMILES Code :	O.Cl.ClC1=CC(=C(N)C=C1)C(C(F)(F)F)=O
MDL No. :	MFCD09841379
InChI Key :	FUYMYLYDBVWEHG-UHFFFAOYSA-N
Pubchem ID :	44181989

Safety of [ 1184936-21-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1184936-21-7 ]

* 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 [ 1184936-21-7 ]

[ 1184936-21-7 ] Synthesis Path-Downstream 1~1

1
[ 383-63-1 ]
[ 65854-91-3 ]
[ 1184936-21-7 ]

Yield	Reaction Conditions	Operation in experiment
42.1 kg (87%)	With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; acetic acid; In hydrogenchloride; hexane; tert-butyl methyl ether;	EXAMPLE 2 Preparation of 4-Chloro-2-trifluoroacetyl-aniline, hydrochloride hydrate N-(4-Chlorophenyl)-2,2-dimethyl propanamide (36.7 kg, 173 mol) was charged to a solution of TMEDA (20.2 kg, 174 mol) in anhydrous t-butyl methyl ether (271.5 kg) and cooled to -20 C. To the cold slurry was added 2.7 N n-butyllithium in hexane (101.9 kg, 393 mol) while keeping the temperature below 5 C. After aging 2 hr at 0 to 5 C., the solution was cooled below -15 C. then rapidly reacted with ethyl trifluoroacetate (34.5 kg, 243 mol). After 30 min, the resulting solution was quenched into 3N HCl (196 L, 589 mol) keeping the temperature below 25 C. After removal of the aqueous phase, the organic solution was concentrated by distilling approximately 200 L of solvent. Acetic acid (352 kg) was added while distilling 325 kg solvent under 100 mm vacuum. After cooling the solution to 30 C., 12 N HCl (43.4 kg, 434 mol) was added and the mixture heated to 65 to 70 C. and held 4 hours. The resulting slurry was cooled to 5 C. and the product was collected by filtration, washed with ethyl acetate (50.5 kg) and dried in vacuo to give 42.1 kg (87%) of the title compound as a white crystalline solid: mp 159-162 dec; 1 H NMR (300 MHz, DMSO-d6) d 7.65-7.5 (complex, 2H), 7.1 (d, J=8 Hz, 1H), 7.0 (brs, 3H); 19 F NMR (282 MHz, DMSO-d6) delta -69.5.
42.1 kg (87%)	With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; acetic acid; In hydrogenchloride; hexane; tert-butyl methyl ether;	EXAMPLE 2 Preparation of 4-Chloro-2-trifluoroacetyl-aniline, hydrochloride hydrate. N-(4-Chlorophenyl)-2,2-dimethyl propanamide (36.7 kg, 173 mol) was charged to a solution of TMEDA (20.2 kg, 174 mol) in anhydrous t-butyl methyl ether (271.5 kg) and cooled to -20 C. To the cold slurry was added 2.7 N n-butyllithium in hexane (101.9 kg, 393 mol) while keeping the temperature below 5 C. After aging 2 hr at 0 to 5 C., the solution was cooled below -15 C. then rapidly reacted with ethyl trifluoroacetate (34.5 kg, 243 mol). After 30 min, the resulting solution was quenched into 3N HCl (196 L, 589 mol) keeping the temperature below 25 C. After removal of the aqueous phase, the organic solution was concentrated by distilling approximately 200 L of solvent. Acetic acid (352 kg) was added while distilling 325 kg solvent under 100 mm vacuum. After cooling the solution to 30 C., 12 N HCl (43.4 kg, 434 mol) was added and the mixture heated to 65 to 70 C. and held 4 hours. The resulting slurry was cooled to 5 C. and the product was collected by filtration, washed with ethyl acetate (50.5 kg) and dried in vacuo to give 42.1 kg (87%) of the title compound as a white crystalline solid: mp 159-162 dec; 1 H NMR (300 MHz, DMSO-d6) d 7.65-7.5 (complex, 2H), 7.1 (d, J =8 Hz, 1H), 7.0 (brs, 3H); 19 F NMR (282 MHz, DMSO-d6) delta-69.5.
42.1 kg (87%)	With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; acetic acid; In hydrogenchloride; hexane; tert-butyl methyl ether;	EXAMPLE 3 Preparation of 4-Chloro-2-trifluoroacetylaniline, hydrochloride hydrate. N-(4-Chlorophenyl)-2,2-dimethyl propanamide (36.7 kg, 173 mol) was charged to a solution of TMEDA (20.2 kg, 174 mol) in anhydrous t-butyl methyl ether (271.5 kg) and cooled to -20 C. To the cold slurry was added 2.7 N n-butyllithium in hexane (101.9 kg, 393 mol) while keeping the temperature below 5 C. After aging 2 hr at 0 to 5 C., the solution was cooled below -15 C. then rapidly reacted with ethyl trifluoroacetate (34.5 kg, 243 mol). After 30 min, the resulting solution was quenched into 3N HCl (196 L, 589 mol) keeping the temperature below 25 C. After removal of the aqueous phase, the organic solution was concentrated by distilling approximately 200 L of solvent. Acetic acid (352 kg) was added while distilling 325 kg solvent under 100 mm vacuum. After cooling the solution to 30 C., 12 N HCl (43.4 kg, 434 mol) was added and the mixture heated to 65 to 70 C. and held 4 hours. The resulting slurry was cooled to 5 C. and the product was collected by filtration, washed with ethyl acetate (50.5 kg) and dried in vacuo to give 42.1 kg (87%) of the title compound as a white crystalline solid: mp 159-162 dec; 1 H NMR (300 MHz, DMSO-d6) d 7.65-7.5 (complex, 2H), 7.1 (d, J=8 Hz, 1H), 7.0 (brs, 3H); 19 F NMR (282 MHz, DMSO-d6) delta-69.5.

42.1 kg (87%)

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; acetic acid; In hydrogenchloride; hexane; tert-butyl methyl ether;

Example 2 Preparation of 4-Chloro-2-trifluoroacetyl-aniline, Hydrochloride Hydrate N-(4-Chlorophenyl)-2,2-dimethyl propanamide (36.7 kg, 173 mol) was charged to a solution of TMEDA (20.2 kg, 174 mol) in anhydrous t-butyl methyl ether (271.5 kg) and cooled to -20 C. To the cold slurry was added 2.7 N n-butyllithium in hexane (101.9 kg, 393 mol) while keeping the temperature below 5 C. After aging 2 hr at 0 to 5 C., the solution was cooled below -15 C. then rapidly reacted with ethyl trifluoroacetate (34.5 kg, 243 mol). After 30 min, the resulting solution was quenched into 3N HCl (196 L, 589 mol) keeping the temperature below 25 C. After removal of the aqueous phase, the organic solution was concentrated by distilling approximately 200 L of solvent. Acetic acid (352 kg) was added while distilling 325 kg solvent under 100 mm vacuum. After cooling the solution to 30 C., 12 N HCl (43.4 kg, 434 mol) was added and the mixture heated to 65 to 70 C. and held 4 hours. The resulting slurry was cooled to 5 C. and the product was collected by filtration, washed with ethyl acetate (50.5 kg) and dried in vacuo to give 42.1 kg (87%) of the title compound as a white crystalline solid: mp 159-162 dec; 1H NMR (300 MHz, DMSO-d6) d 7.65-7.5 (complex, 2H), 7.1 (d, J=8 Hz, 1H), 7.0 (brs, 3H); 19F NMR (282 MHz, DMSO-d6) delta -69.5.

References: [1]Patent: US5925789,1999,A .
[2]Patent: US5932726,1999,A .
[3]Patent: US6028237,2000,A .
[4]Patent: US6673372,2004,B1 .

Historical Records

Technical Information

• Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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CAS No.: 1184936-21-7

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