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Chemical Structure| 167405-28-9 Chemical Structure| 167405-28-9

Structure of 167405-28-9

Chemical Structure| 167405-28-9

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Product Details of [ 167405-28-9 ]

CAS No. :167405-28-9
Formula : C6H5F3N2OS
M.W : 210.18
SMILES Code : CC(C1=C(C(F)(F)F)N=C(N)S1)=O
MDL No. :MFCD18711443
InChI Key :WATJHCODYKTHLP-UHFFFAOYSA-N
Pubchem ID :18936300

Safety of [ 167405-28-9 ]

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

Application In Synthesis of [ 167405-28-9 ]

* 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 [ 167405-28-9 ]

[ 167405-28-9 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 167405-28-9 ]
  • [ 75-36-5 ]
  • [ 860620-59-3 ]
YieldReaction ConditionsOperation in experiment
90% With pyridine; In tetrahydrofuran; dichloromethane; at 0 - 20℃; 1- [2-amino-4- (trifluoromethyl)-1, 3-thiazol-5-yl] ethanone, obtained in Step I as described above (1 g, 5.7 mmol), is dissolved in a mixture of THF (7.5 mL), DCM (7. 5 mL) and pyridine (1 g, 12.8 mmol). The resulting solution is cooled down to 0 C and acetylchloride (0.6 g, 7.7 mmol) is added. The mixture is stirred overnight at RT. It is diluted with water (10 mL) and extracted with DCM (3*25 mL). The combined organic phase is washed with water, brine, dried over MgS04, filtrated and concentrated. The resulting crude product, N- [5-acetyl-4-(trifluoromethyl)-1, 3-thiazol-2-yl) acetamide, is used in the next step without further purification (l. lg, 90%).
  • 2
  • [ 17356-08-0 ]
  • [ 167405-28-9 ]
YieldReaction ConditionsOperation in experiment
79% Hydroxy (tosyloxy) iodobenzene (3g, 7. 7mmol) is added to a solution of 1, 1, 1,-trifluoro pentane-2,4-dione (1 g, 6.4 mmol) in ACN (10 mL). The resulting mixture is heated under reflux for 45 minutes, then cooled down to RT, and thiourea (0.59 g, 7.7 mmol) is added. The mixture is heated under relfux for 4 hours and then left to stand overnight. The reaction mixture is concentrated and the residue is recrystallised in ethylacetate and petroleum ether, affording 1- [2-amino-4- (trifluoromethyl)-1, 3-thiazol-5-yl] ethanone (P8) as white solid (1.2 g, 79%).
  • 3
  • 3-guanidinobenzoate ethyl ester nitrate [ No CAS ]
  • [ 167405-28-9 ]
  • [ 1188-33-6 ]
  • [ 752245-59-3 ]
YieldReaction ConditionsOperation in experiment
A mixture 5-ACETYL-2-AMINO-4-TRIFLUOROMETHYLTHIAZOLE (prepared according to wo95/01979) (2.02 g, 9.6 mmol) in N, N-dimethylformamide diethyl acetal (15 mL) is heated to reflux for 3 hours. The reaction mixture is cooled to room temperature, concentrated and hexane (20 mL) is added. The solid is collected by filtration and washed with hexane and dried. A mixture of the above solid, 3-ethoxycarbonyl-phenyl-guanidine nitrite (2.75 g, 10.2 mmol), lithium hydroxide (240 mg, 10.1 mmol) in 2-butanol (40 mL) is heated to reflux overnight. The reaction mixture is cooled to room temperature, solvent is removed and water (40 mL) is added. The resultant solid is collected by filtration and washed with water, isopropanol and dried to give N-[3-ethoxycaqrbonyl-phenyl]- 4-(2-amino-4-trifluoromethyl- 5-THIAZOLYL)-2-PYRIMIDINEAMINE (3.5 g); ESI-MS (M/Z) : 410.1 (M++ H).
  • 4
  • [ 167405-28-9 ]
  • [ 1377581-61-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide; bromine; In 1,4-dioxane; water; at 60℃; for 2h; Intermediate 6: Step c 1-(2-Amino-4-trifluoromethyl-thiazol-5-yl)-2-bromo-ethanone A solution of bromine (0.024 mL, 0.475 mmol) in dioxane (3 mL) was added dropwise to a solution of <strong>[167405-28-9]1-(2-amino-4-trifluoromethyl-thiazol-5-yl)-ethanone</strong> (0.100 g, 0.475 mmol, intermediate 6, step b) in 48% aqueous HBr (3 mL) at 60 C. and stirred for 2 hours. The reaction mixture was cooled to room temperature, saturated aqueous NaHCO3 was added slowly and the pH was adjusted to 7 with 2 N aqueous Na2CO3. Ethyl acetate was added and the product was extracted, dried with sodium sulfate and evaporated to give the title compound.
With bromine; In 1,4-dioxane; ethyl acetate; Intermediate 6: step c 1-(2-Amino-4-trifluoromethyl-thiazol-5-yl)-2-bromo-ethanone A solution of bromine (0.024 mL, 0.475 mmol) in dioxane (3 mL) was added dropwise to a solution of <strong>[167405-28-9]1-(2-amino-4-trifluoromethyl-thiazol-5-yl)-ethanone</strong> (0.100 g, 0.475 mmol, intermediate 6, step b) in 48% aqueous HBr (3 mL) at 60 C. and stirred for 2 hours. The reaction mixture was cooled to room temperature, saturated aqueous NaHCO3 was added slowly and the pH was adjusted to 7 with 2 N aqueous Na2CO3. Ethyl acetate was added and the product was extracted, dried with sodium sulfate and evaporated to give the title compound.
  • 5
  • [ 367-57-7 ]
  • [ 167405-28-9 ]
  • 6
  • [ 1377581-59-3 ]
  • [ 167405-28-9 ]
YieldReaction ConditionsOperation in experiment
With thiourea; In dichloromethane; ethyl acetate; acetonitrile; Intermediate 6: step b 1-(2-Amino-4-trifluoromethyl-thiazol-5-yl)-ethanone A solution of toluene-4-sulfonic acid 1-acetyl-3,3,3-trifluoro-2-oxo-propyl ester (0.100 g, 0.308 mmol, intermediate 6, step a) and thiourea (0.028 g, 0.370 mmol) in acetonitrile (5 mL) were heated to reflux for several hours. The reaction mixture was then cooled to room temperature and evaporated. Ethyl acetate was added and the solution was filtered. The filtrate was evaporated, dichloromethane was added and the solution was filtered to give the title compound as a solid.
 

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