Home Cart Sign in  
Chemical Structure| 421-52-3 Chemical Structure| 421-52-3

Structure of 2,2,2-Trifluorothioacetamide
CAS No.: 421-52-3

Chemical Structure| 421-52-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 421-52-3 ]

CAS No. :421-52-3
Formula : C2H2F3NS
M.W : 129.10
SMILES Code : S=C(N)C(F)(F)F
MDL No. :MFCD02093844
InChI Key :VZBAIMIVLDKBTE-UHFFFAOYSA-N
Pubchem ID :4425751

Safety of [ 421-52-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H315-H319-H332-H335
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P322-P330-P332+P313-P337+P313-P340-P362-P363-P403-P403+P233-P405-P501

Application In Synthesis of [ 421-52-3 ]

* 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 [ 421-52-3 ]

[ 421-52-3 ] Synthesis Path-Downstream   1~35

  • 3
  • [ 354-38-1 ]
  • [ 421-52-3 ]
YieldReaction ConditionsOperation in experiment
95% With tetraphosphorus decasulfide; In tetrahydrofuran; at 70 - 75℃; for 4h;Inert atmosphere; Commercially available trifluoroacetamide(39.9842g, 0.353717 mol) powderStir at room temperature with 400 mL THF in a 1000 mL 2-neck-round flask.Then phosphorous pentasulfide (31.4482 g, 0.141486 mol)Add powder and reflux Flow N2 gas while stirring. At this time to maintain 70 ~ 75 for reflux and stirred for 4 hours. After the reaction is finished,After evaporating the solvent with the rotary evaporator, remove the by-product white solid with THF and then distillation.Through yellow liquid form trifluorothioamide(43.38 g, 95.0%) was obtained.
65% With Lawessons reagent; In tetrahydrofuran; for 2h;Reflux; A mixture of Trifluoroacetamide (1.2 g, 10.6 mmol), Lawesson's reagent (2.36 g, 5.84 mmol) and THF (10 mL) was heated at reflux for 2 h.The mixture was concentrated and purified by chromatography to give the sub-title compound (0.89 g, 6.9 mmol, 65 %).
With Lawessons reagent; In brief, thioamides INT-2a,b required for thiazole synthesis can be prepared by reacting the corresponding amides INT-1a,b with Lawesson's reagent.
With Lawessons reagent; In tetrahydrofuran; for 18h;Heating / reflux; A solution of 2,2,2 -trifluoroacetamide (7.12 g, 63 mmol) and Lawesson's Reagent (15.3 g, 37.8 mmol) in THF (60 ml) was stirred at reflux for 18 h. The reaction mixture was cooled, ethyl bromopyruvate (8 ml, 63 mmol) added and the reaction refluxed for 18 h. The reaction was cooled, evaporated in vacuo, and the resulting crude material extracted into ethyl acetate and washed with water. The organic fraction was dried over MgSO4 and condensed to give a yellow/orange oil. The oil was purified by flash column chromatography on silica eluting with 15 % ethyl acetate in hexane to provide the title compound as a clear oil (3 g, 21 %). 1H NMR (400 MHz, CDCl3) delta 8.39 (1 H, s), 4.47 (2 H, q, J7.1), 1.42 (3 H, t, J7.2).
With Lawessons reagent; In tetrahydrofuran; for 6h;Reflux; Intermediate 49Ethyl 2-(trifluoromethyl)-1 ,3-thiazole-4-carboxylate To a solution of 2,2,2-trifluoroacetamide (5g) in THF (50ml) was added Lawesson's reagent (9g) and the mixture heated at reflux for 6h. The mixture was cooled to RT overnight. The solvent was concentrated to a volume of 20ml and this was diluted with DCM (60ml). This solution was purified by chromatography on silica gel (3x50g cartridges) eluting with DCM. The clean fractions were combined and the impure product containing fractions combined. The impure fractions were concentrated to a volume of 20ml and purified by chromatography on silica gel (5Og cartridge) eluting with DCM. All the clean product containing fractions were combined and concentrated in vacuo to give 2,2,2- trifluoroethanethioamide as a dark yellow oil. A portion of this oil (1g) was suspended in anhydrous ethanol (20ml) and bromoethylpyruvate (0.97ml) added. This mixture was heated at reflux for 18h. The mixture was cooled and then poured into water (50ml) and the pH adjusted to -8 by the addition of solid sodium bicarbonate. The ethanol was <n="112"/>removed in vacuo and the resultant aqueous solution extracted with ethyl acetate (3x50ml). The combined organic extracts were dried over sodium sulphate and concentrated in vacuo. Purification by chromatography on silica gel (2Og cartridge) eluting with DCM gave the title compound (0.358g) as an orange solid. LC/MS Rt2.83min m/z 226 [MH+]. Method A

  • 4
  • [ 100-46-9 ]
  • [ 421-52-3 ]
  • [ 7387-69-1 ]
  • 8
  • [ 177561-18-1 ]
  • [ 421-52-3 ]
  • [ 177561-43-2 ]
  • 9
  • [ 71006-38-7 ]
  • [ 421-52-3 ]
  • [ 177561-23-8 ]
  • 12
  • [ 4341-76-8 ]
  • [ 421-52-3 ]
  • ethyl (2-trifluoromethyl-4,5-dihydrothiazol-5-yl)acetate [ No CAS ]
  • 13
  • [ 762-42-5 ]
  • [ 421-52-3 ]
  • [ 860481-08-9 ]
  • 14
  • [ 109-76-2 ]
  • [ 421-52-3 ]
  • [ 672-39-9 ]
  • 15
  • [ 110-60-1 ]
  • [ 421-52-3 ]
  • [ 672-60-6 ]
  • 16
  • [ 416860-00-9 ]
  • [ 421-52-3 ]
  • C20H17F3N2O3S [ No CAS ]
  • 17
  • [ 416860-02-1 ]
  • [ 421-52-3 ]
  • C14H13F3N2OS [ No CAS ]
  • 18
  • [ 363-58-6 ]
  • [ 421-52-3 ]
  • ethyl 2,4-bis-trifluoromethyl-5-thiazole carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In water; ethyl acetate; acetonitrile; Step 3 - Preparation of ethyl 2,4-bis-trifluoromethyl-5-thiazole carboxylate: To a 3L 4-neck RBF equipped with a mechanical stirrer, reflux condenser, thermometer and addition funnel was charged 358 g of ethyl chlorotrifluoroacetoacetate (1.64 moles), 2,2,2-<strong>[421-52-3]trifluorothioacetamide</strong> and 1000 mL of acetonitrile. To this mixture was added 331.9 g of triethylamine (2.0 eq, 3.28 moles) dropwise over 2.5 hours. During the addition the temperature was maintained at 30-38 C and upon completion of the addition the reaction was heated to reflux for 2 hours and stirred overnight at room temperature. The reaction mixture was filtered and the resulting filtrate was concentrated by rotary evaporation to provide an oily solid which was dissolved in 1500 mL of ethyl acetate. This was washed with 2 x 500 mL of water, 1 x 500 mL of brine and concentrated by rotary evaporation to yield 356.6 g of ethyl 2,4-bis-trifluoromethyl-5-thiazole carboxylate which was purified by distillation.
  • 19
  • [ 19172-47-5 ]
  • [ 354-38-1 ]
  • [ 421-52-3 ]
YieldReaction ConditionsOperation in experiment
84% Step 1 - Preparation of trifluorothioacetamide: To a 1L 4-neck round bottom flask (RBF), equipped with a mechanical stirrer, nitrogen inlet, addition funnel and thermometer, was charged trifluoroacetamide (56.0 grams (g), 1.0 equiv. 0.495 mole) and 100 g of Lawesson's reagent followed by 500 milliliters (mL) of tetrahydrofuran. The reaction mixture was heated to boiling for 2 hours. The solvent was carefully removed by rotary evaporation to yield 86 g of crude product. This material was distilled by kugelrohr distillation under high vacuum (<1 mm Hg) to afford 54 g of light yellow liquid trifluorothioacetamide (84% yield).
  • 20
  • [ 363-58-6 ]
  • [ 421-52-3 ]
  • ethyl 2,4-bis-trifluoromethyl-5-thiazole carboxylate [ No CAS ]
  • 2,4-bis-trifluoromethylthiazole-5-carboxvlic acid chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In acetonitrile; Step 3 - Preparation of ethyl 2,4-bis-trifluoromethyl-5-thiazole carboxylate: To a 3L 4-neck RBF equipped with a mechanical stirrer, reflux condenser, thermometer and addition funnel was charged 358 g of ethyl chlorotrifluoroacetoacetate (1.64 moles), 2,2,2-<strong>[421-52-3]trifluorothioacetamide</strong> and 1000 mL of acetonitrile. To this mixture was added 331.9 g of triethylamine (2.0 eq, 3.28 moles) dropwise over 2.5 hours. During the addition the temperature wasmaintained at 30-38 C and upon completion of the addition the reaction was heated to reflux for 2 hours and stirred overnight at room temperature. The reaction mixture was filtered and the resulting filtrate was concentrated by rotary evaporation to provide an oily solid which was dissolved in 1500 mL of ethyl acetate. This was washed with 2 x 500 mL of water, 1 x 500 mL of brine and concentrated by rotary evaporation to yield 356.6 g of ethyl 2,4-bis-trifluoromethyl-5-thiazole carboxylate which was purified by distillation.
  • 21
  • [ 70-23-5 ]
  • [ 421-52-3 ]
  • [ 133046-46-5 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; for 18h;Heating / reflux; A solution of 2,2,2 -trifluoroacetamide (7.12 g, 63 mmol) and Lawesson's Reagent (15.3 g, 37.8 mmol) in THF (60 ml) was stirred at reflux for 18 h. The reaction mixture was cooled, ethyl bromopyruvate (8 ml, 63 mmol) added and the reaction refluxed for 18 h. The reaction was cooled, evaporated in vacuo, and the resulting crude material extracted into ethyl acetate and washed with water. The organic fraction was dried over MgSO4 and condensed to give a yellow/orange oil. The oil was purified by flash column chromatography on silica eluting with 15 % ethyl acetate in hexane to provide the title compound as a clear oil (3 g, 21 %). 1H NMR (400 MHz, CDCl3) delta 8.39 (1 H, s), 4.47 (2 H, q, J7.1), 1.42 (3 H, t, J7.2).
  • 27
  • [ 20375-16-0 ]
  • [ 421-52-3 ]
  • [ 936129-78-1 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile;Reflux; Production Example 26; A solution of ethyl 3-chloro-2-oxo-3-phenylpropanoate and <strong>[421-52-3]trifluorothioacetamide</strong> in MeCN was heated under reflux. To the reaction mixture was added an aqueous Na2CO3 solution, followed by extraction with EtOAc. The organic layer was washed with water and brine in this order, dried, and then concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane: EtOAc) to obtain ethyl 5-phenyl-2-(trifluoromethyl)-1,3-thiazole-4-carboxylate as a white solid.
  • 28
  • [ 513-81-5 ]
  • [ 421-52-3 ]
  • [ 1214893-14-7 ]
YieldReaction ConditionsOperation in experiment
35% In 1-methyl-pyrrolidin-2-one; at 85℃; for 3h;Microwave irradiation; General procedure: A stirring bar and one piece of Weflon (Weflon is Teflon filled with graphite) were placed in a 10 mL pressure vessel. Thioamide 9g (0.25 g, 1 mmol), N-methylpyrrolidin-2-one (NMP) (3 mL), and 2,3-dimethylbuta-1,3-diene (3) (0.56 mL, 5 mmol) were then added. The tube was sealed with a Teflon septum and heated in CEM Discover microwave reactor (reaction parameters: standard mode, T=180 C, muW power: 300 W, running time: 30 min). After one run, another portion of 1,3-diene 3 (0.28 mL, 2.5 mmol) was added with a syringe through the septum and reaction mixture was heated again under the same conditions. Addition of new portions of diene and heating were continued until 19F NMR of reaction mixture showed maximum conversion (total heating time: 3 h, 1,3-diene: 15-20 equiv, see Table 1). The reaction mixture was then poured into water (50 mL) and extracted with CH2Cl2 (3×25 mL). The combined organic phases were washed with water (30 mL), dried over MgSO4, evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: mixture petroleum ether (PE) and ethyl acetate, 9:1). Combined fractions containing 10g were evaporated and redissolved in MeOH (5-10 mL) to precipitate impurities of polymerized diene. After filtration and solvent evaporation, pure compound 10g (0.16 g, 49%) was obtained as a colorless oil (Scheme 2, Table 1: entry 7).
  • 29
  • [ 376-71-6 ]
  • [ 421-52-3 ]
  • [ 1384866-37-8 ]
YieldReaction ConditionsOperation in experiment
84% at 100℃; for 1h; General procedure: A mixture of polyfluoroalkanethioamide (1a-c) (10.0 mol, 1.0 equiv.) and 2,2,3,3,4,4,5,5-octafluoropentanoyl chloride (30.0 mol, 3.0 equiv.) was heated at 100 C for 1 h. The crude product was purified by fractional distillation to give the corresponding NH-acyl derivative (4a-c).
  • 30
  • [ 98-88-4 ]
  • [ 421-52-3 ]
  • [ 1384866-42-5 ]
YieldReaction ConditionsOperation in experiment
50% at 100℃; General procedure: A mixture of polyfluoroalkanethioamide (1a-c) (20.0 mmol, 1.0 eqiuv.) and the corresponding acyl chloride (40.00 mmol, 2.0 eqiuv.) was heated at 100 C for 13-25 h. After the completion of the reaction, the excess of acyl chloride was removed in vacuo (0.08 mmHg). The crude product was purified by recrystallization from ethanol. N-[1-(benzoyldithio)-2,2,3,3-tetrafluoro-propyl]benzamide (6b) was purified by column chromatography on silica gel (eluent:mixture (70:30) of ethyl acetate and hexane).
  • 31
  • [ 75-36-5 ]
  • [ 421-52-3 ]
  • N,N'-[2,4-bis(trifluoromethyl)-1,3-dithitane-2,4-diyl]diacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; In acetonitrile; at -20 - 20℃;Inert atmosphere; General procedure: A solution of acetyl chloride (21.0 mmol, 1.4 eqiuv.) in acetonitrile (10 mL) was added dropwise at -20 C under argon atmosphere to a solution of the corresponding polyfluoroalkanethioamide (15.0 mmol, 1.0 eqiuv.) (1a-c) and pyridine (21.0 mmol, 1.4 eqiuv.) in acetonitrile (40 mL). The reaction mixture was stirred at -20 C for 0.5 h and then for 16 h at room temperature. The solvent was evaporated in vacuo at room temperature and diethyl ether (50 mL) was added to the residue. In the case of the isolation of compound (3), the precipitate formed was filtered off, washed with water (10 mL) and dried. For the isolation of compounds (2b,c) the precipitate was filtered off and the filtrate was washed with water (3 × 10 mL). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo giving NH-acetyl derivatives (2b,c).
  • 32
  • [ 2491-36-3 ]
  • [ 421-52-3 ]
  • [ 1402003-85-3 ]
YieldReaction ConditionsOperation in experiment
49% In ethanol;Reflux; Step 1. Synthesis of 2-[2-(trifluoromethyl)-1,3-thiazol-4-yl]phenol (C4) 2,2,2-Trifluoroethanethioamide (which may be prepared by the method of J. H. Hillhouse et al., Phosphorus, Sulfur Relat. Elem. 1986, 26, 169-84) (157 mg, 1.22 mmol) in ethanol (1.3 mL) was added drop-wise to a solution of 2-bromo-1-(2-hydroxyphenyl)ethanone (119 mg, 0.55 mmol) in ethanol (1.3 mL) and the reaction was refluxed overnight. The reaction was concentrated in vacuo and purified via silica gel chromatography (Gradient: 5% to 20% ethyl acetate in heptane) to afford the title compound. Yield: 67 mg, 0.27 mmol, 49%. LCMS m/z 246.0 (M+1). 1H NMR (400 MHz, CDCl3) delta 6.95 (ddd, J=8, 7, 1 Hz, 1H), 7.07 (dd, J=8.2, 1.2 Hz, 1H), 7.33 (ddd, J=8, 7, 2 Hz, 1H), 7.64 (dd, J=7.8, 1.6 Hz, 1H), 7.81 (s, 1H), 10.47 (s, 1H).
  • 33
  • [ 1363381-55-8 ]
  • [ 421-52-3 ]
  • [ 1421938-81-9 ]
YieldReaction ConditionsOperation in experiment
49% Example 14c (racemic mixture)Oxalyl chloride (410 mu, 4.84 mmol) and a drop of DMF are added to racemic 3- azabicyclo[3.1.0]hexane-l,3-dicarboxylic acid-3-tert-butyl ester (1000 mg, 4.40 mmol) in DCM (12 mL) cooled to 0C. After stirring at that temperature for 2h, ACN (12 mL) followed by trimethylsilyldiazomethane in hexanes (2M, 4.4 mL, 8.80 mmol) are added dropwise. The reaction mixture is stirred at 0C for 2h and then at room temperature overnight. The reaction mixture is then cooled to 0C, hydrobromic acid (48%, 989 mu, 8.80 mmol) is added dropwise and stirring is continued at rt for 10 min. Solid NaHC03 is added until basic pH and stirring is continued for 5 min. The reaction mixture is diluted with EtOAc, washed with water and saturated NaHC03, brine, dried over Na2SC"4 and evaporated under reduced pressure to obtain a residue, 980 mg. 200 mg of such residue are mixed with <strong>[421-52-3]2,2,2-trifluoroethanethioamide</strong> (170 mg, 1.31 mmol) in EtOH (1 mL) and heated at 70C overnight. Volatiles are evaporated under reduced pressure and the resulting residue purified by flash chromatography (eluent 10% EtOAc/cyclohexane) to furnish the title compound (146 mg, 49%>).HPLC-MS (Method 2): Rt =1.48 minMS (ESI pos): m/z = 279 (M-tBu+H)+
  • 34
  • C12H19NO3 [ No CAS ]
  • [ 421-52-3 ]
  • C14H17F3N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 70℃; Oxalyl chloride (410 mul, 4.84 mmol) and a drop of DMF are added to racemic 3-azabicyclo[3.1.0]hexane-1,3-dicarboxylic acid-3-tert-butyl ester (1000 mg, 4.40 mmol) in DCM (12 mL) cooled to 0 C. After stirring at that temperature for 2 h, ACN (12 mL) followed by trimethylsilyldiazomethane in hexanes (2M, 4.4 mL, 8.80 mmol) are added dropwise. The reaction mixture is stirred at 0 C. for 2 h and then at room temperature overnight. The reaction mixture is then cooled to 0 C., hydrobromic acid (48%, 989 mul, 8.80 mmol) is added dropwise and stirring is continued at rt for 10 min Solid NaHCO3 is added until basic pH and stirring is continued for 5 min. The reaction mixture is diluted with EtOAc, washed with water and saturated NaHCO3, brine, dried over Na2SO4 and evaporated under reduced pressure to obtain a residue, 980 mg. 200 mg of such residue are mixed with <strong>[421-52-3]2,2,2-trifluoroethanethioamide</strong> (170 mg, 1.31 mmol) in EtOH (1 mL) and heated at 70 C. overnight. Volatiles are evaporated under reduced pressure and the resulting residue purified by flash chromatography (eluent 10% EtOAc/cyclohexane) to furnish the title compound (146 mg, 49%). HPLC-MS (Method 2): Rt=1.48 min. MS (ESI pos): m/z=279 (M-tBu+H)+
  • 35
  • [ 609-15-4 ]
  • [ 421-52-3 ]
  • [ 1263286-63-0 ]
YieldReaction ConditionsOperation in experiment
133 mg In tert-butyl alcohol; at 20℃; for 48h; To a mixture of 2 , 2 , 2-trifluoroethanethioamide (200 mg) and t-BuOH (10 mL) was added ethyl 2-chloro-3-oxqbutanoate (0.217 mL) at room temperature. The mixture was refluxed for 2 days. After cooling, EtOAc was poured into the mixture, and the mixture was washed successively with water and brine, dried over a2S04 and concentrated in vacuo. The residue was purified by silica gel column chromatography (NH, EtOAc/hexane) to give the title compound (133 mg) . XH NMR (300 MHz, CDC13) delta 1.39 (3H, t, J = 7.16 Hz), 2.79 (3H, s) , 4.38 (2H, q, J = 6.91 Hz)
 

Historical Records

Technical Information

Categories