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Structure of 886361-30-4

Chemical Structure| 886361-30-4

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Product Details of [ 886361-30-4 ]

CAS No. :886361-30-4
Formula : C11H9FN2O2S
M.W : 252.27
SMILES Code : O=C(C1=C(C2=CC=C(F)C=C2)SC(N)=N1)OC
MDL No. :MFCD06200913

Safety of [ 886361-30-4 ]

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

Application In Synthesis of [ 886361-30-4 ]

* 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 [ 886361-30-4 ]

[ 886361-30-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 160727-95-7 ]
  • [ 17356-08-0 ]
  • [ 886361-30-4 ]
YieldReaction ConditionsOperation in experiment
In acetone; at 57℃; for 24.0h; A solution of the respective alpha-oxo-ester (22.1 mmol, 1.0 eq) in acetone (25 mL) is added to a suspension of thiourea (22.1 mmol, 1.0 eq) in acetone (45 mL). The mixture is heated to 57 C. (bath temperature), stirred for 24 h and concentrated to half of the volume. The obtained suspension is filtered and the residue is washed with acetone. After drying the desired amino-thiazole derivative is obtained as a solid.
In acetone; at 57℃; for 24.0h; A.l.5.2 Synthesis of 2-amino-thiazole-4-carboxylic acid methyl ester derivatives (general procedure Hantzsch 2); A solution of the respective alpha-oxo-ester (22.1 mmol, 1.0 eq) in acetone (25 mL) is added to a suspension of thiourea (22.1 mmol, 1.0 eq) in acetone (45 mL). The mixture <n="48"/>is heated to 57C (bath temperature), stirred for 24 h and concentrated to half of the volume. The obtained suspension is filtered and the residue is washed with acetone.After drying the desired amino-thiazole derivative is obtained as a solid.2-Amino-5-(4-fluoro-phenyl)-thiazole-4-carboxylic acid methyl ester prepared by reaction of 3-chloro-2-oxo-(4-fluoro-phenyl)-propionic acid methyl ester with thiourea. LC-MS: tR = 0.75 min; [M+H]+ = 253.17.2-Amino-5-(4-methyl-phenyl)-thiazole-4-carboxylic acid methyl ester prepared by reaction of 3-chloro-3-(4-methyl-phenyl)-2-oxo-propionic acid methyl ester with thiourea. LC-MS: tR = 0.77 min; [M+H]+ = 249.28. 2-Amino-5-(3-methoxy-phenyl)-thiazole-4-carboxylic acid methyl ester prepared by reaction of 3-chloro-3-(3-methoxy-phenyl)-2-oxo-propionic acid methyl ester with thiourea. LC-MS: tR = 0.75 min; [M+H]+ = 265.25.2-Amino-5-(3-chloro-phenyl)-thiazole-4-carboxylic acid methyl ester prepared by reaction of 3-chloro-3-(3-chloro-phenyl)-2-oxo-propionic acid methyl ester with thiourea. LC-MS: tR = 0.82 min; [M+H]+ = 269.18.2-Amino-5-(2-fluoro-phenyl)-thiazole-4-carboxylic acid methyl ester prepared by reaction of 3-chloro-3-(2-fluoro-phenyl)-2-oxo-propionic acid methyl ester with thiourea. LC-MS: tR = 0.76 min; [M+H]+ = 253.20.2-Amino-5-(3-trifluoromethyl-phenyl)-thiazole-4-carboxylic acid methyl ester prepared by reaction of 3-chloro-3-(3-trifluoromethyl-phenyl)-2-oxo-propionic acid methyl ester with thiourea. LC-MS: tR = 0.86 min; [M+H]+ = 303.28.
  • 2
  • [ 886361-30-4 ]
  • [ 1038508-94-9 ]
YieldReaction ConditionsOperation in experiment
With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 5 - 65℃; for 2.0h; In an inert atmosphere, copper(II)bromide (69.6 mmol, 1.0 eq) was suspended in acetonitril (300 ml) and cooled to 5-100C followed by the addition of 3- methylbutylnitrite (104 mmol, 1.45 eq) over 15 min. To this reaction mixture the respective 2-aminothiazole derivative (70.0 mmol, 1 eq, free amine) was added in portions over 20 min. at 5-100C. The reaction mixture was then carefully heated to 65C and stirring continued for 2 h. The volatiles were removed under reduced pressure and the residue was purified by column chromatography (silicagel; heptan / EtOAc or DCM / methanol, as the appropriate mixture) to give the respective product. 2-bromo-5-(4-fluoro-phenyl)-thiazole-4-carboxylic acid methyl ester prepared by reaction of <strong>[886361-30-4]2-amino-5-(4-fluoro-phenyl)-thiazole-4-carboxylic acid methyl ester</strong>. LC-MS: tR = 0.97 min; [M+H]+ = 316.1.
With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 5 - 65℃;Inert atmosphere; In an inert atmosphere, copper(II)bromide (47.3 mmol, 1.0 eq) was suspended in MeCN (200 mL) and cooled to 5-10 C. followed by the addition of 3-methylbutylnitrite (71 mmol, 1.45 eq) over 15 min. To this reaction mixture the respective 2-aminothiazole derivative (47.3 mmol, 1 eq) was added in portions over 35 min at 5-10 C. The reaction mixture was then carefully heated to 65 C. and stirring continued for 2 h. The volatiles were removed under reduced pressure and the black residue was purified by FC (heptane/EtOAc, as the appropriate mixture) to give the products as slightly yellow oils or solids
With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 5 - 65℃; for 2.33333h;Inert atmosphere; A.1.4 Synthesis of 2-bromo-thiazole-4-carboxylic acid methyl ester Derivatives (General Procedure); In an inert atmosphere, copper(II)bromide (69.6 mmol, 1.0 eq) was suspended in acetonitril (300 ml) and cooled to 5-10 C. followed by the addition of 3-methylbutylnitrite (104 mmol, 1.45 eq) over 15 min. To this reaction mixture the respective 2-aminothiazole derivative (70.0 mmol, 1 eq, free amine) was added in portions over 20 min. at 5-10 C. The reaction mixture was then carefully heated to 65 C. and stirring continued for 2 h. The volatiles were removed under reduced pressure and the residue was purified by column chromatography (silicagel; heptan/EtOAc or DCM/methanol, as the appropriate mixture) to give the respective product.; 2-bromo-5-(4-fluoro-phenyl)-thiazole-4-carboxylic acid methyl esterprepared by reaction of <strong>[886361-30-4]2-amino-5-(4-fluoro-phenyl)-thiazole-4-carboxylic acid methyl ester</strong>. LC-MS: tR=0.97 min; [M+H]+=316.1.
With isopentyl nitrite;copper(ll) bromide; In acetonitrile; at 5 - 65℃; for 2.83333h; A.l.5.3 Synthesis of 2-bromo-thiazole-4-carboxylic acid methyl ester derivatives (general procedure Sandmeyer)Sandmeyer- reaction In an inert atmosphere, copper(II)bromide (47.3 mmol, 1.0 eq) was suspended in MeCN (200 mL) and cooled to 5-100C followed by the addition of 3-methylbutylnitrite (71 mmol, 1.45 eq) over 15 min. To this reaction mixture the respective 2-aminothiazole derivative (47.3 mmol, 1 eq) was added in portions over 35 min at 5-100C. The reaction mixture was then carefully heated to 65C and stirring continued for 2 h. The volatiles <n="49"/>were removed under reduced pressure and the black residue was purified by FC(heptane / EtOAc, as the appropriate mixture) to give the products as slightly yellow oils or solids.2-Bromo-5-(4-fluoro-phenyl)-thiazole-4-carboxylic acid methyl ester LC-MS: tR = 0.97 min; [M+H]+ = 316.09.2-Bromo-5-(4-methyl-phenyl)-thiazole-4-carboxylic acid methyl esterLC-MS: tR = 1.00 min; [M+H]+ = 314.25.2-Bromo-5-(3-methoxy-phenyl)-thiazole-4-carboxylic acid methyl esterLC-MS: tR = 0.97 min; [M+H]+ = 330.20. 2-Bromo-5-(3-chloro-phenyl)-thiazole-4-carboxylic acid methyl esterLC-MS: tR = 1.00 min; [M+H]+ = 332.17.2-Bromo-5-(2-fluoro-phenyl)-thiazole-4-carboxylic acid methyl esterLC-MS: tR = 0.96 min; [M+H]+ = 316.11.2-Bromo-5-(3-trifluoromethyl-phenyl)-thiazole-4-carboxylic acid methyl ester LC-MS: tR = 1.03 min; [M+H]+ = 366.17.

  • 4
  • [ 886361-30-4 ]
  • [ 124-63-0 ]
  • [ 1422176-17-7 ]
YieldReaction ConditionsOperation in experiment
77% With pyridine; at 60℃; To a solution of P-29 (1g, 3.96mmol) in pyridine (10 mL) was added methanesulfonyl chloride (0.62mL, 7.92mmol) and the resulting mixture was stuffed at 60C over night. Reaction mixture was then brought to room temperature and pyridine was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated aq. sodium bicarbonate, water and brine. Organic layer was dried with anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (hexanes/ethyl acetate) to afford 1g (77%) of product 12. To a stuffed suspension of intermediate 2 (1g, 3mmol) was added 2M LiOH in dioxane (7.5mL, 3mmol) and the solution was stirred for 2h at 40C. The reaction mixture was then gradually acidified with 1N HCl. Diluted with water and extracted with ethyl acetate. Organic layer was washed with brine and dried with anhydrous sodium sulfate. Filtration and evaporation of organic layer afforded 0.9g (94%) of the product S-29.
  • 5
  • [ 886361-30-4 ]
  • [ 1422175-27-6 ]
  • 6
  • [ 886361-30-4 ]
  • [ 1038508-87-0 ]
 

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