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Chemical Structure| 79455-63-3 Chemical Structure| 79455-63-3

Structure of 79455-63-3

Chemical Structure| 79455-63-3

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Product Details of [ 79455-63-3 ]

CAS No. :79455-63-3
Formula : C7H3Cl2FO
M.W : 193.00
SMILES Code : O=C(Cl)C1=C(F)C=CC=C1Cl
MDL No. :MFCD00178746
InChI Key :GFNAJZAKJGKJCS-UHFFFAOYSA-N
Pubchem ID :2736547

Safety of [ 79455-63-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H227-H290-H314
Precautionary Statements:P210-P234-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P370+P378-P390-P403+P235-P405-P406-P501
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 79455-63-3 ]

* 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 [ 79455-63-3 ]

[ 79455-63-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 777-12-8 ]
  • [ 79455-63-3 ]
  • N-(6-trifluoromethylbenzothiazol-2-yl)-2-chloro-6-fluorobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; dmap; In water; EXAMPLE 2 STR7 At 0 to 5° C., 2-chloro-6-fluorobenzoyl chloride (1.93 g) was added dropwise to a solution composed of 2-amino-6-trifluoromethylbenzothiazole (2.18 g), pyridine (30 ml) and 4-dimethylaminopyridine (0.1 g). The reaction mixture was stirred at room temperature (20 to 30° C.) for one day, and then the pyridine was evaporated. Water was added to the residue, and the mixture was stirred. The resulting crystals were collected by filtration, and thoroughly washed with water. Recrystallization from ethanol gave the desired N-(6-trifluoromethylbenzothiazol-2-yl)-2-chloro-6-fluorobenzamide (2.5 g). mp. 265°-270° C.
  • 2
  • [ 159783-22-9 ]
  • [ 79455-63-3 ]
  • [ 1365992-45-5 ]
  • [ 1365992-46-6 ]
YieldReaction ConditionsOperation in experiment
2-Chloro-6-fluorobenzoyl chloride (13.6 g, 71.6 mmol) was added dropwise, over 10 minutes, to a solution of <strong>[159783-22-9]3,5-difluoro-pyridin-4-ylamine</strong> (7.7 g, 59.3 mmol) in pyridine (100 mL) at 0 C under argon and the reaction mixture was stirred at 0 C for 3 hours. The volatiles were removed under reduced pressure and the resultant residue was treated with IN HCl (100 mL). The resultant suspension was stirred at room temperature for 2 hours and then the solid was collected by filtration, washing with water. A mixture of 2-chloro-N-(3,5-difluoropyridin-4-yl)-6- fluorobenzamide, LCMS (Method E): RT = 2.83 min, m/z: 287 [M+H+], and of 2-chloro-N-(2-chloro-6- fluorobenzoyl)-N-(3,5-difluoropyridin-4-yl)-6-fluorobenzamide LCMS (Method E): RT = 3.96 min, m/z: 443 [M+H+], (23 g) was obtained which was used in the following step without further purification.A suspension of the crude mixture (23 g) and 1M NaOH (200 mL) in MeOH (200 mL) was stirred at room temperature for 2 hours. Additional amounts of 1M NaOH (200 mL) and of MeOH (200 mL) were added and stirring at room temperature was continued for 2 hours and then at 80 C for 1 hour. After cooling to room temperature, the mixture was made acidic by addition of cone HCl (33 mL). The suspension was evaporated in vacuo to half of the original volume and the residue was collected by filtration, washed with water and dried to afford the title compound as a cream solid (11.6 g, 68%). LCMS (Method E): RT = 2.76 min, m/z: 287 [M+H+].
  • 3
  • [ 1214326-89-2 ]
  • [ 79455-63-3 ]
  • [ 1365993-01-6 ]
YieldReaction ConditionsOperation in experiment
49% To a solution of 3-bromo-5- fluoro-pyridin-4-amine (20.0 mmol, 3.82 g) in DMF (40 niL) was added NaH (40.0 mmol, 1.6 g).The mixture was stirred at room temperature for 30 min, then cooled to 0 C. A soluntion of 2-chloro-6-fluoro-benzoyl chloride (30.0 mmol, 5.79 g) in DCM (10 niL) was then added dropwise. The reaction mixture was stirred at room temperature for 16 hours. The reaction was then quenched with ice water, extracted with EtOAc. The combined organics were dried (Na2S04), filtered and concentrated.The resultant oil was dissolved in MeOH (40 mL) and THF (40 mL). 2N NaOH (30 mL) was added. The mixture was stirredat room temperature for 16 hours. The volatile solvents were then removed under reduced pressure. Water (100 mL) was added. The aqueous layer was saturated with NaCl, extracted with CHCL/zPrOH (3/1). The combined organics were dried (Na2S04), filtered and concentrated. The crude product was purified by silica gel chromatography (0-8% EtOAc/DCM) to give the title compound as an off- white solid (3.4 g, 49% yield). ¾ NMR (400 MHz, DMSO) delta 11.07 (s, IH), 8.74 (s, IH), 8.71 (s, IH), 7.59 (dd, J= 14.8, 7.8 Hz, IH), 7.47 (d, J= 8.1 Hz, IH), 7.40 (t, J= 8.6 Hz, IH). LCMS (ESI) m z 348.9 [M+H+].
 

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