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CAS No. : | 863127-76-8 | MDL No. : | MFCD13185963 |
Formula : | C12H14ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DBYFNZJHXGNAGW-BQYQJAHWSA-N |
M.W : | 239.70 | Pubchem ID : | 44557928 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.6% | With pyridine; In tetrahydrofuran; at 0 - 20℃; for 2h; | To a cold stirring solution of 2-chloro-6-methylaniline (59.5 g 0.42 mol) and pyridine (68 ml, 0.63 mol) in THF (600 mL) was added 3-ethoxyacryloyl chloride (84.7 g, 0.63 mol) slowly keeping the temp at 0-5C. The mixture was then warmed and stirred for 2 h. at 20C. Hydrochloric acid (1N, 115 mL) was added at 0-10C. The mixture was diluted with water (310 mL) and the resulting solution was concentrated under vacuum to a thick slurry. The slurry was diluted with toluene (275 mL) and stirred for 15 min. at 20-22C then 1 h. at 0C. The solid was collected by vacuum filtration, washed with water (2 x 75 mL) and dried to give 74.1 g (73.6 % yield) of (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide). lH NMR (400 Hz, DMSO-d6) 8 1. 26 (t, 3H, J= 7 Hz), 2.15 (s, 3H), 3.94 (q, 2H, J= 7 Hz), 5.58 (d, 1H, J=12.4 Hz), 7.10-7. 27 (m, 2H, J=7.5 Hz), 7.27-7. 37 (d, 1H, J=7.5 Hz), 7.45 (d, 1H, J=12.4 Hz), 9. 28 (s, 1H) ; l3c NMR (100MHz, CDC13) b : 14. 57, 18.96, 67.17, 97.99, 126. 80, 127. 44, 129. 07, 131.32, 132.89, 138. 25,161. 09,165. 36. |
300 g | With pyridine; In tetrahydrofuran; at 10 - 30℃; for 4h; | Ethyl vinyl ether compound of formula-5 (500 gm) was slowly added to oxalyl chloride compound of formula-4 (670 ml) at 10-15C. Raised the temperature of the reaction mixture to 25-30C and stirred for 12 hours at the same temperature. Heated the reaction mixture to 120- 125C and stirred for 90 minutes at the same temperature. Cooled the reaction mixture to 30-35 C and (E)-3-ethoxyacryloyl chloride compound of formula-7 was collected by fractional distillation. Added tetrahydrofuran (1160 ml) to the obtained compound of formula-7 and cooled the reaction mixture to 10-15C. Slowly added a solution of 2-methyl-6-chloroaniline compound of formula-9 (290 gm), pyridine (248ml) & tetrahydrofuran (1160 ml) to the reaction mixture at same temperature. Raised the temperature of the reaction mixture to 25-30C and stirred the reaction mixture for 4 hours at the same temperature. Cooled the reaction mixture to 5-10C and acidified the reaction mixture using aqueous HC1 solution. Water and ethyl acetate were added to the reaction mixture and stirred for 10 minutes. Separated the both aqueous & organic layers and extracted the aqueous layer with ethyl acetate. Washed the total organic layer with aqueous sodium bicarbonate solution followed by with water. Distilled off the solvent completely from the organic layer under reduced pressure. Ethyl acetate was added to the obtained compound at 25-30C and cooled the reaction mixture to 0-5C. Stirred the reaction mixture for 2 hours at the same temperature. Filtered the precipitated solid, washed with chilled ethyl acetate and dried the material to get the title compound. Yield: 300 gm; M.R.: 160-164C; HPLC Purity: 99.66%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.8% | 23.9 g (100 mmol) of N- (2-chloro-6-methylphenyl) -3-ethoxyacrylamide was mixed with 7.2 g (35 mmol) of iodine monobromide at room temperature,And 10.9 g (50 mmol) of 1-butyl-3-methylimidazolium bromide were added to a flask and stirred in 120 ml of THFAnd the temperature was raised to 40 C. 22.8 g (300 mmol) of thiourea was added to the mixture obtained by the above-mentioned mixingThe reaction was stirred for 1.5 hours, cooled to room temperature, poured into ice water, extracted with methylene chloride, the organic phase was concentrated, washed with water and then ethanolAnd then dried to obtain 26.4 g of 2-amino-N- (2-chloro-6-methylphenyl) thiazole-5-carboxamide in a yield of 98.8%purity99.61%. | |
90% | Example 2; [0164] To a mixture of compound 1 (5.30 g, 22.1 1 mmol) in 1 ,4-dioxane (100 mL) and water (70 mL) was added NBS (4,40 g, 24,72 mmol) at -10 to 0C. The slurry v/as warmed and stirred <n="55"/>at 20-22C, for 3 h. Thiourea (1 ,85 g, 26, 16 mmol) was added and the mixture heated to 100C. After 2 h, the resulting solution was cooled to 20-22C and cone, ammonium hydroxide (6 mL) was added dropwise. The resulting slurry was concentrated under vacuum to about half volume and cooled to 0-5 "C. The solid was collected by vacuum filtration, washed with cold water, and dried to give 5.4 g (90% yield) of compound 2 as deep-yellow solids, 1H NMR (500 MHz1 DMSOd6) delta 2, 19 (s, 3H), 7.09-7.29 (m, 2H, J=7,5), 7.29-7,43 (d, IH, J=7,5), 7.61 (s, 2H)1 7,85 (s, IH)1 9.63 (s, IH); ESI-MS: calcd for (Cl 1H10C1N3OS) 267, found 268 MH+), | |
90% | Example 2[0157] To a mixture of compound 1 (5.30 g, 22.11 mmol) in 1,4-dioxane (100 mL) and water (70 mL) was added NBS (4.40 g, 24.72 mmol) at -10 to 0 C. The slurry was warmed and stirred at 20-22 C for 3 h. Thiourea (1.85 g, 26.16 mmol) was added and the mixture heated to 100 C. After 2 h, the resulting solution was cooled to 20-22 C and cone, ammonium hydroxide (6 mL) was added drop wise. The resulting slurry was concentrated under vacuum to about half volume and cooled to 0-5 C. The solid was collected by vacuum filtration, washed with cold water, and dried to give 5.4 g (90% yield) of compound 2 as deep-yellow solids. 1H NMR (500 MHz, DMSO-d6) delta 2.19 (s, 3H), 7.09-7.29 (m, 2H, J=7.5), 7.29-7.43 (d, IH, J=7.5), 7.61 (s, 2H), 7.85 (s, IH), 9.63 (s, IH); ESI-MS: calcd for (C?HioClN3OS) 267, found 268 MH+). |
213 g | E)-<strong>[863127-76-8]N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide</strong> compound of formula-8 (240 gm) was added to a mixture of N-bromosuccinimide (267.1 gm), water (960 ml) and 1,4-dioxane (480 ml) at 25-30C and stirred the reaction mixture for 3 hours at the same temperature. Thiourea (76.8 gm) was added to the reaction mixture at 25-30C. Heated the reaction mixture to 65-70C and stirred for 2 hours at the same temperature. Cooled the reaction mixture to 15-20C. The reaction mixture was added slowly to a pre-cooled (15-20C) aqueous ammonia solution (600 ml of ammonia in 960 ml of water) at 15-20C and stirred the reaction mixture for 2 hours at same temperature. Filtered the precipitated solid and washed with water. Water was added to the obtained compound and stirred for 40 minutes at 25-30C. Filtered the precipitated solid, washed with water and dried to get the title compound. Yield: 213 gm; MR.: 195-200C; HPLC Purity: 98.77%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In tetrahydrofuran; at 20℃; | Example 1; [0163] A mixture of ethyl beta-ethoxyacrylate (26.50 g, 183 rnmol) and 2 N sodium hydroxide(110 mL, 220 mrnol) was refluxed for 2 h and cooled to 0C , water was removed under vacc, and the yellow solids were triturated with toluene and evaporated to give the sodium beta- ethoxyacrylate (25 g, 97%). The mixture of sodium beta-thoxyacrylate (10.26 g, 74.29 mrnol) and thionyl chloride (25 mL, 343 mmol) was refluxed for 2 h, and evaporated, to give the beta- ethoxyacryloyl chloride crude product, which was used without purification, To a cold stirring solution of 3-ethoxyacryloyl chloride in THF (100 mL) was added 2-chloro-6-methylaniline (6.2 mL, 50,35 mmol) and pyridine (9 ml, 1 1 1 mmol) The mixture was then wanned and stirred overnight at room temperature. Water was added at 0-10C, extracted with EtOAc, The organic layer was washed with CuSO4 (3x50 mL) and the resulting solution was passed a pad of silica gel, concentrated under vacuum to give solids, The solids was diluted with toluene and kept, at 0C, The solid was collected by vacuum filtration, washed with water and dried to give 5,2 g (43% yield) of compound 1 , (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide). 1H NMR (500 Hz1 CDCl3) delta 1 ,26 (t, 3H1 J=7 Hz), 2, 15 (s, 3H), 3 94 (q, 2H, J=7 Hz), 5,58 (d, IH, J=12.4 Hz), 7.10-7.27 (m, 2H, J=7.5 Hz), 7,27-7.37 (d, IH, J=7.5 Hz), 7,45(d, 1Hf J=12.4 Hz); ESI-MS: calcd for (Cl 2H14C1NO2) 239, found 240 MH+), | |
With pyridine; In tetrahydrofuran; at 20℃; | Example 1[0156] A mixture of ethyl beta-ethoxyacrylate (26.50 g, 183 mmol) and 2 N sodium hydroxide (110 mL, 220 mmol) was refluxed for 2 h and cooled to 0 C water was removed under vacc, and the yellow solids were triturated with toluene and evaporated to give the sodium beta-ethoxyacrylate (25 g, 97%). The mixture of sodium beta-thoxyacrylate (10.26 g, 74.29 mmol) and thionyl chloride (25 mL, 343 mmol) was refluxed for 2 h, and evaporated, to give the beta-ethoxyacryloyl chloride crude product, which was used without purification. To a cold stirring solution of 3-ethoxyacryloyl chloride in THF (100 mL) was added 2-chloro-6- methylaniline (6.2 mL, 50.35 mmol) and pyridine (9 ml, 111 mmol). The mixture was then warmed and stirred overnight at room temperature. Water was added at 0-10 C, extracted with EtOAc. The organic layer was washed with CuSO4 (3x50 mL) and the resulting solution was passed a pad of silica gel, concentrated under vacuum to give solids. The solids was diluted with toluene and kept, at O0C. The solid was collected by vacuum filtration, washed with water and dried to give 5.2 g (43% yield) of compound 1, (E)-N-(2-chloro-6- methylphenyl)-3-ethoxyacrylamide). 1H NMR (500 Hz, CDCl3) delta 1.26 (t, 3H, J=7 Hz), 2.15 (s, 3H), 3.94 (q, 2H, J=7 Hz), 5.58 (d, IH, J=12.4 Hz), 7.10-7.27 (m, 2H, J=7.5 Hz), 7.27- 7.37 (d, IH, J=7.5 Hz), 7.45(d, IH, J=12.4 Hz); ESI-MS: calcd for (C12Hi4ClNO2) 239, found 240 MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Example 35 [0190] To a mixture of compound 1 (180 g, 0.75 mmol) in 1,4-dioxane (3 mL) and water (3 mL) was added NBS (160 mg, 0.90mmol) at 0 C. The slurry was warmed and stirred at 20-22 C for 3 h. Urea (58 mg, 0.97 mmol) was added and the mixture heated to 100 C. After 2 h, the resulting solution was cooled to 20-22 C and cone, ammonium hydroxide (0.2 mL) was added dropwise. The resulting slurry was concentrated under vacuum. The remaining water was removed by co-evaporating with toluene. The residue was purified by column chromatography on silica gel (0-6% 2N ammonia in methanol/100-94% dichloromethane) to give compound 35 as white solids. (120 mg, 63% yield). 1H NMR (500 MHz, DMSO-d6) delta 9.57 (s, IH), 7.60 (s, IH), 7.36 (d, J = 7.5 Hz, IH,), 7.31 (s, 2H), 7.09- 7.29 (m, 2H), 2.19 (s, 3H); ESI-MS: calcd for (Ci .H10ClN3O2) 251, found 252 (MH+), 250 ([M-H]"). |
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