41507-35-1|3-Thiophenecarbonylchloride| Ambeed

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Yield	Reaction Conditions	Operation in experiment
84%	at 0 - 20℃; for 0.5 h;	Diethylamine (28.0 mL, 271.82 mmol) and 160 mL CH₂Cl₂ were mixed at 0 °C, and the solution of 1 was added into the reagent slowly. After all of the 1 solution was added, the reactant was stirred at room temperature for 30 min. Then, the reactant was washed by water (3*60 mL), and the organic layer was dried over Na₂SO₄. After removing solvent, the crude product was purified by distillation under vacuum, and pale yellow oil was obtained in 84percent yield. ¹H NMR (400 MHz, CDCl₃) δ (ppm): 7.47 (s, 1H), 7.33-7.31 (m, 1H), 7.18 (d, J=4.0 Hz, 1H), 3.51-3.29 (m, 4H), 1.23-1.17 (m, 6H).
58%	at 20℃; for 0.5 h;	500mL was added a diethylamine (60 mL) in a round flask, it allows to install the Ice-base. Then, thiophene-3-carbonyl chloride (compound g-1) gives a slow infusion by dissolving in 10mL of methylene chloride. After stirring at room temperature for 30 minutes, after extraction via the methylene chloride and aqueous NaCl solution, extracting the organic solvent to give a dark yellow liquid (N, N- diethyl-3-thiophene carboxamide amide (compound g-2) and (yield: 58percent).

1
[ 41507-35-1 ]
[ 64-17-5 ]
[ 5751-80-4 ]

Reference： [1]Journal of the American Chemical Society,1948,vol. 70,p. 1555,1557
Org. Synth. Coll.,1963,vol. Vol. IV,p. 919

2
[ 88-13-1 ]
[ 41507-35-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With oxalyl dichloride In dichloromethane for 1.91667h; Inert atmosphere; Reflux;
91%	With oxalyl dichloride In dichloromethane at 0 - 20℃;
78%	With oxalyl dichloride In dichloromethane at 0℃; for 12h;	7 Preparation of Thiophene-3-carbonyl chloride (compound g-1) 250mL thiophene-3-carboxylic Acid into a tea (5g) in a round flask, 100mL of methylene chloride is injected. After slowly inject (9mL) oxalyl chloride at 0 °C, it stirred for 12 hours. After 12 hours, removing the organic solvent, it is possible to obtain a yellow liquid (thiophene-3-carbonyl chloride (compound g-1)). (Yield: 78%)

75%	With dichlorosulfoxide In N,N-dimethyl-formamide at 20℃; for 12h;	1 Preparation of thiophene-3-carbonyl chloride In a 500 mL three-necked flask, thiophene-3-carboxylic acid (12.8 g, 0.1 mol) was dissolved in N,N-dimethylformamide, and 20 ml of thionyl chloride was added dropwise to the reaction solution, and the mixture was stirred at room temperature for 12 hours. After that, the reaction was stopped, the reaction was quenched with water, extracted with methylene chloride and dried over anhydrous magnesium sulfate, and then concentrated to give a pale yellow solid, purified by silica gel column chromatography, petroleum ether / dichloromethane /1, v/v) was the eluent to give a white solid, yield 75%. The results of 1H NMR, 13C NMR, MS and elemental analysis indicated that the obtained compound was the target product, and the chemical reaction equation of the preparation process was as follows:
53%	With dichlorosulfoxide In benzene for 2h; Reflux;
	With dichlorosulfoxide
	With dichlorosulfoxide for 1h; Heating;
	With dichlorosulfoxide In dichloromethane
	With dichlorosulfoxide for 2h; Heating;
	With dichlorosulfoxide for 18h; Ambient temperature;
	With dichlorosulfoxide In chloroform for 3h; Heating;
	With dichlorosulfoxide for 0.25h; Heating;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane
	With dichlorosulfoxide at 50℃; for 0.75h;
	With dichlorosulfoxide In N,N-dimethyl-formamide; toluene for 1h; Heating;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;
	With dichlorosulfoxide for 2h; Heating;
	With dichlorosulfoxide In toluene at 115℃; for 3h;
	With dichlorosulfoxide
	With dichlorosulfoxide In chloroform for 2h; Heating / reflux;	26 Thiophene-3-carboxylate (10 g, 78 mmol) was dissolved in chloroform (500 ml), treated with thionyl chloride (6.83 ml, 93.6 mmol) and heated to reflux for 2 hours. This solution was then added by cannulation to a solution of Weinreb Amine (11.4 g, 117 mmol) and triethylamine (30 ml, 210.6 mmol) in chloroform (100 ml). The reaction was then stirred at room temperature overnight. The solvent was reduced in vacuo to 100 ml, washed with water (150 ml), dried (Na2SO4) and concentrated. The resulting orange oil was purified by vacuum distillation (150 ° C. at 5 mbar) to give the title compound as a pale yellow oil (8.50 g, 64%). MS (ES+) 172. δH (d6 DMSO): 3.25 (3H, s), 3.64 (3H, s), 7.43 (1H, d), 7.56 (1H, d), 8.25 (1H, s).
	With dichlorosulfoxide	14 2,2'-Benzo[1,2-b:4,5-b']dithiophen-4,8-diyldioxy)bis-N,N-diethyl ethylamine, dihydrochloride A 100 g. portion of thionyl chloride is added to 34.8 g. of 3-thiophene carboxylic acid. This mixture is stirred and warmed on a steam bath for 15 minutes, then heated at reflux for 45 minutes. The excess thionyl chloride is distilled off and the remaining reaction mixture is fractionated at 32-36 mm. pressure, giving 34.0 g. of 3-thiophene carbonyl chloride.
	With dichlorosulfoxide	19.a (a) (a) 3-Thiophenecarboxylic acid chloride 5.12 g (44 mmol) of 3-thiophenecarboxylic acid are added to 50 ml of thionyl chloride, the mixture is heated to boiling for 2 h and then evaporated, the residue is taken up with toluene and the latter is evaporated off. 5 g of residue are obtained, this being used without further treatment in the following stage.
	With dichlorosulfoxide	6 EXAMPLE 6 EXAMPLE 6 Thiophene-3-carboxylic acid is converted to the acid chloride by reaction with thionyl chloride. Thiophene-3-carbonyl chloride is isolated by distillation at 80°-85° C./0.25 mm.
	With dichlorosulfoxide at 20℃; for 12h;
	With dichlorosulfoxide In toluene Reflux;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;	55 Oxalyl chloride (2 mmol) and DMF (2 drops) were added sequentially to a stirred solution of the corresponding acid (1.5 mmol) in CH2C12 at room temperature, then further stirred for 2 h under argon atmosphere. The solvent was removed under vacuum at room temperature to yield corresponding acid chloride. A solution of 1- benzyl-2-oxo-4-piperazin-1-yl-1, 2-DIHYDRO- [1, 8]-NAPHTHYRIDINE-3-CARBOXYLIC acid ethyl ester (5) (392 mg, 1 mmol) in dry pyridine (5 mL) was added to the residue under argon atmosphere and briefly sonicated. The solution was stirred overnight at room temperature under argon atmosphere. The solution was poured into ice water and the solids formed were filtered. The solids were washed by excess water, dried, and purified by flash chromatography eluting with 0-2 % MEOH in a CH2C12 gradient. ; Synthesis of 1-Benzyl-2-oxo-4-[4-(thiophene-3-carbonyl)-piperazin-1-yl]-1,2- DIHYDRO- [1, 8]-NAPHTHYRIDINE-3-CARBOXYLIC acid ethyl ester (55) [0334] The compound was prepared according to general method D. White solid, yield 68 %, mp 115 °C. 1H-NMR (DMSO-D6) : d 1.29 (t, J= 7.2 Hz, 3H), 3.14 (b, 4H), 3.75 (b, 4H), 4.30 (q, J= 7.2 Hz, 2H), 5.56 (s, 2H), 7.25 (m, 6H), 7. 37 (m, 1H), 7.65 (m, 1H), 7. 85 (dd, J= 1.2, 2.8 Hz, 1H), 8.34 (dd, J= 2.0, 8. 0 Hz, 1H), 8.67 (dd, J= 2.0, 4.8 Hz, 1H) ; EIMS m/z 503 (M+1).
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane
	With dichlorosulfoxide at 20℃; for 16h;
	With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran for 1h; Inert atmosphere;
	With dichlorosulfoxide In benzene
	With dichlorosulfoxide; N,N-dimethyl-formamide In toluene for 16h;	5.2.1. General procedure for the synthesis of acid chlorides (2a-f, 5a-c) General procedure: Heterocyclic carbolic acids refPreviewPlaceHolder[23], refPreviewPlaceHolder[24] and refPreviewPlaceHolder[25] (1 equiv) were suspended in dry toluene (150 mL) at room temperature. Thionyl chloride (5 equiv) was added dropwise. The reaction mixtures were stirred for 5 min at room temperature and then DMF (3-5 drops) was added. The mixtures were stirred for 16 h and then evaporated to dryness. The residues were used directly in the next step.
	With dichlorosulfoxide at 85℃; for 2h;
	With dichlorosulfoxide Heating;
	With oxalyl dichloride In dichloromethane
	With dichlorosulfoxide for 1h; Reflux;
	With oxalyl dichloride In dichloromethane
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; Inert atmosphere;
	With dichlorosulfoxide In dichloromethane at 0 - 50℃; for 3h;	11.A Step A: N-methoxy-N-methylthiophene-3-carboxamide To a stirred solution of thiophene-3-carboxylic acid (20 g, 1.0 eq) in CH2C12 at 0 °C was added SOCl2 (59 mL, 5.2 eq). After gas evolution became less vigorous, the reaction mixture was refluxed for 3 h at 50 °C. The mixture was then concentrated and the residue was used directly in the next step without further purification. N, O-dimethylhydroxylamine hydrochloride (16.8 g, 1.1 eq) was added to a solution of the above residue in CH2C12 at 0 °C, then to the resulting solution was added dropwise Et3N (44 mL, 2.0 eq). The mixture was stirred at rt for 3 h, washed with water, and extracted by CH2C12. The extract was dried, concentrated, and purified by column chromatography with petroleum ether:EtOAc = 5: 1 to give the desired product as a yellow solid (17.2 g, 64% yield). :H NMR (400 MHz, CDC13) δ 8.07 (s, 1H), 7.57 (d, J = 8.8 Hz, 1H), 7.28 (d, J = 8.4 Hz, 1H), 3.65 (s, 3H), 3.36 (s, 3H).
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;	General Procedure for amide formation from carboxylic acids General procedure: Oxalyl dichloride (21 mmol, 1.05 equiv) was added to asuspension of the carboxylic acid (20 mmol, 1 equiv) in CH2Cl2(50 mL) at room temperature. A drop of DMF was added and the reaction stirredat room temperature for 1 h (bubbling ceased and the reaction becomes homogeneousduring this period). The volatiles were removed under vacuum, then the oilyresidue was dissolved in CH2Cl2 (50 mL) and cooled in anice-bath. The amine (20 mmol, 1 equiv) and triethylamine (22 mmol, 1.1 equiv)were added in CH2Cl2 (10 mL), and the reaction wasstirred for 30 min, before warming to room temperaure. The solution was washedwith sat. NH4Cl solution and brine, then dried over MgSO4,filtered and concentrated to give the following amides, which were used withoutfurther purification.
	With dichlorosulfoxide at 80 - 90℃; for 1h;
	With oxalyl dichloride In dichloromethane at 0℃;
	With dichlorosulfoxide In N,N-dimethyl-formamide for 1h; Reflux;	General procedure: It was prepared by two-step process. In a typical experiment, 2-thiophene carboxylicacid was placed in a 100 ml single-necked round-bottom flask fitted with a double wallreflux condenser and a calcium chloride guard tube. Thionyl chloride (1.09 ml, 0.0075 mol)and few drops of N,N-dimethylformamide were added to the flask and refluxed for 1 hour.The excess thionyl chloride was removed by vacuum pump. Then it was dissolved in ethylmethyl ketone (50 ml) and added dropwise through pressure equalizing dropping funnelfor 45 minutes at 0C to the mixture of 4-hydoxy phenyl 4-(dodecyloxy) benzoate (2 g,0.005 mol) and triethylamine (0.84 ml, 0.006 mol) in ethyl methyl ketone. The reactionmixture was allowed for stirring for 5 hours. Then the flask was taken out, the triethylaminesalt was filtered, and the solvent was removed from solution under reduced pressure. Thesolid obtained was washed twice with 2% potassium hydroxide solution followed by waterand then dried, recrystallized from isopropyl alcohol and methanol.Similar protocols were used for synthesizing other homologues of the series.
	With dichlorosulfoxide for 3h; Reflux;
	With dichlorosulfoxide In N,N-dimethyl-formamide; toluene at 20℃;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere; Schlenk technique;
	With dichlorosulfoxide; N,N-dimethyl-formamide for 1h; Reflux;	Synthesis of 3- thiophene carbonyl chloride General procedure: Synthesis of 2 or 3- thiophene carbonyl chloride (6). 2 (or) 3- thiophene carboxylicacid (3 g, 0.0234 mol) which was placed in a 100 ml single neck round bottomed flask fittedwith a double wall reflux condenser and a calcium chloride guard tube. Thionyl chloride(2.13 ml, 0.0292 mol) and a few drops of DMF were added to the flask. The reactionmixture was refluxed for about one hour and the excess SOCl2 was removed by vacuumpump.
	With dichlorosulfoxide In dichloromethane; N,N-dimethyl-formamide at 60℃; for 5h; Inert atmosphere;
	With oxalyl dichloride In dichloromethane at 20℃;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃;

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3
[ 41507-35-1 ]
[ 62-32-8 ]
C₁₉H₁₇NO₄S₂*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In trifluoroacetic acid for 4h; Ambient temperature;

Reference： [1]Casagrande; Santangelo; Saini; Doggi; Gerli; Cerri [Arzneimittel-Forschung/Drug Research, 1986, vol. 36, # 2 A, p. 291 - 303]

4
[ 41507-35-1 ]
[ 456-00-8 ]
[ 99923-42-9 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 333 - 341

5
[ 41507-35-1 ]
[ 7120-43-6 ]
Thiophene-3-carboxylic acid 5-chloro-2-hydroxy-benzoylamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2196 - 2201

6
[ 41507-35-1 ]
[ 109-89-7 ]
[ 73540-75-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	In dichloromethane; at 0 - 20℃; for 0.5h;	Diethylamine (28.0 mL, 271.82 mmol) and 160 mL CH2Cl2 were mixed at 0 C, and the solution of 1 was added into the reagent slowly. After all of the 1 solution was added, the reactant was stirred at room temperature for 30 min. Then, the reactant was washed by water (3*60 mL), and the organic layer was dried over Na2SO4. After removing solvent, the crude product was purified by distillation under vacuum, and pale yellow oil was obtained in 84% yield. 1H NMR (400 MHz, CDCl3) delta (ppm): 7.47 (s, 1H), 7.33-7.31 (m, 1H), 7.18 (d, J=4.0 Hz, 1H), 3.51-3.29 (m, 4H), 1.23-1.17 (m, 6H).
58%	In dichloromethane; at 20℃; for 0.5h;	500mL was added a diethylamine (60 mL) in a round flask, it allows to install the Ice-base. Then, thiophene-3-carbonyl chloride (compound g-1) gives a slow infusion by dissolving in 10mL of methylene chloride. After stirring at room temperature for 30 minutes, after extraction via the methylene chloride and aqueous NaCl solution, extracting the organic solvent to give a dark yellow liquid (N, N- diethyl-3-thiophene carboxamide amide (compound g-2) and (yield: 58%).
	In dichloromethane; at 10 - 35℃;Inert atmosphere; Cooling with ice;	Diethylamine and the 3-thiophenoyl chloride prepared in step (a) are respectively dissolved in methylene chloride,The amine is dissolved in methylene chloride and the 3-thiophenoyl chloride prepared in step (a) is dissolved in another dichloromethane;The solution of 3-thiophenoyl chloride was added to the diethylamine solution under ice-cooling to remove the ice bath at 10 to 35 C.After 1 to 3 hours, N, N-diethylthiophene-3-carboxamide (N, N-diethylthiophene-3-carboxamide) was obtained.

Reference： [1]Journal of Materials Chemistry A,2016,vol. 4,p. 18409 - 18415
[2]Tetrahedron,2016,vol. 72,p. 2219 - 2225
[3]Macromolecules,2014,vol. 47,p. 1008 - 1020
[4]New Journal of Chemistry,2015,vol. 39,p. 2248 - 2255
[5]Patent: KR101495152,2015,B1 .Location in patent: Paragraph 0184; 0188-0189
[6]Journal of Medicinal Chemistry,1997,vol. 40,p. 1585 - 1599
[7]Doklady Chemistry,2011,vol. 440,p. 257 - 262
[8]Macromolecules,2012,vol. 45,p. 8628 - 8638
[9]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1527 - 1532
[10]RSC Advances,2014,vol. 4,p. 44902 - 44910
[11]Journal of the American Chemical Society,2015,vol. 137,p. 1448 - 1451
[12]Organic electronics,2015,vol. 25,p. 245 - 253
[13]Chemistry - A European Journal,2015,vol. 21,p. 16252 - 16265
[14]Patent: CN105968124,2016,A .Location in patent: Paragraph 0013; 0014
[15]Chemistry - A European Journal,2019,vol. 25,p. 14870 - 14880

7
[ 41507-35-1 ]
[ 21617-15-2 ]
7-Chloro-1-(thiophene-3-carbonyl)-2,3-dihydro-1H-quinolin-4-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1998,vol. 33,p. 267 - 277

8
[ 41507-35-1 ]
[ 67-56-1 ]
[ 22913-26-4 ]

Reference： [1]Archiv der Pharmazie,1998,vol. 331,p. 405 - 411

9
[ 41507-35-1 ]
[ 5098-14-6 ]
5-amino-2-thiophen-3-yl-oxazole-4-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 2898 - 2908

10
[ 41507-35-1 ]
[ 358-23-6 ]
[ 2555-30-8 ]
[ 121-44-8 ]
2-oxo-4-phenyl-2H-chromen-7-yl trifluoromethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane	27.2 Step 2: Step 2: 4-Phenyl-7-trifluoromethanesulfonyloxycoumarin To a solution of 7-hydroxy-4-phenylcoumarin from Step 1 (1.22 g) and Et3 N (1.05 mL) in CH2 Cl2 (25 mL) at 0° C. was added trifluoro-methanesulfonic anhydride (1.6 g). After 30 min., the mixture was poured onto 1N HCl, extracted (3x EtOAc), washed with brine, dried, and evaporated. Purification on silica gel (hexane/EtOAc 2:1) gave the title compound.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US5360815, 1994, A

11
[ 41507-35-1 ]
[ 2555-30-8 ]
[ 121-44-8 ]
2-oxo-4-phenyl-2H-chromen-7-yl trifluoromethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethanesulfonic acid anhydride In dichloromethane	27.2 Step 2: Step 2: 4-Phenyl-7-trifluoromethanesulfonyloxycoumarin To a solution of 7-hydroxy-4-phenylcoumarin from Step 1 (1.22 g) and Et3 N (1.05 mL) in CH2 Cl2 (25 mL) at 0° C. was added trifluoromethanesulfonic anhydride (1.6 g). After 30 min., the mixture was poured onto 1N HCl, extracted 3*EtOAc, washed with brine, dried and evaporated. Purification on silica gel (hexane/EtOAc 2:1) gave the title compound.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US5424320, 1995, A

12
[ 41507-35-1 ]
[ 4949-69-3 ]
[ 623907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; potassium carbonate; In dichloromethane; at 0 - 20℃; for 19h;	Example 7; N-(3-{8-(2.6-DifluorophenylV7-oxo-2-r(2,2,6.6-tetramethyl-4-piperidinyl')aminol-5,6,7, 8-tetrahydropyrimido[4,5-(/1pyrimidin-4-yl\|-4-methylphenyl)-3- thiophenecarboxamide; 7a) N-Q -iodo-4-methyrphenyl)-3 -thiophenecarboxamide; 3-Thiophenecarboxylic acid (2.O g, 15.6 mmol) was dissolved in methylene chloride (100 mL) and 2 drops of DMF were added. The mixture was cooled to 0 0C and oxalyl chloride (1.5 mL, 17.1 mmol) was added slowly and allowed to warm to room temperature. Gas evolution was observed during warming. 3-Methyl-4- iodoaniline (5.45 g, 23.5 mmol), 4 drops of pyridine and K2CO3 (2.58 g, 18.7 mmol) are dissolved in CH2Cl2 (10 mL) and cooled to about 00C. After about Ih, the acid chloride mixture is slowly added to the cooled aniline mixture and allowed to warm to room temperature and stirred for about 18h. The resulting mixture is filtered, washed with ethyl acetate and the filtrate is concentrated to a brown oil. The crude EPO <DP n="125"/>material was purified via flash chromatography (10-30% ethyl acetate in hexanes) to afford the title compound (1.56 g, 29%) as an off-white solid.

Reference： [1]Patent: WO2006/104889,2006,A2 .Location in patent: Page/Page column 123-124

13
[ 41507-35-1 ]
[ 404827-77-6 ]
[ 1279846-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; at 25℃; for 16h;	6-Bromo-1-[(thiophen-2-yl)carbonyl]-3-[(thiophen-2-yl)carbonylamino]indazole; A solution of 10 g of 6-bromo-3-amino-1H-indazole in 250 mL of pyridine is admixed with 13.8 g of 3-thiophenecarboxylic chloride. The reaction mixture is stirred under an argon atmosphere for 16 hours at a temperature close to 25 C. and then poured into 400 mL of water. The suspension is then filtered and the product is washed with 2×80 mL of water, treated with suction and dried, to give 19.27 g of 6-bromo-1-[(thiophen-2-yl)carbonyl]-3-[(thiophen-2-yl)carbonylamino]indazole, whose characteristics are as follows: MS spectrum (ES+): m/z=433 [MH+]

Reference： [1]Patent: US2007/161626,2007,A1 .Location in patent: Page/Page column 7-8

14
[ 41507-35-1 ]
[ 718632-46-3 ]
C₂₀H₂₆N₄O₅S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 1844 - 1853

15
[ 41507-35-1 ]
[ 132559-91-2 ]
[ 1357190-59-0 ]

Reference： [1]Synlett,2011,p. 2867 - 2871

16
[ 41507-35-1 ]
[ 28657-75-2 ]
[ 1240861-50-0 ]

Yield	Reaction Conditions	Operation in experiment
80.8%	With triethylamine In toluene at 20℃; for 48h;	5.2.2. General procedure for the synthesis of carboxamides (3a-j and 6a-e) General procedure: Into separate solutions of acid chlorides (2a-f, 5a-c) in 150 mL dry toluene at room temperature were added 2,3,4-substituted-6-amino acetophenones (1a-c) refPreviewPlaceHolder[14], refPreviewPlaceHolder[26] and refPreviewPlaceHolder[27] (1.1 equiv). The reaction mixtures were stirred and then triethylamine (3 mL) was added dropwise. The mixtures were stirred at room temperature for 48 h and then evaporated. The residues were isolated by chromatography, and then recrystallization gave the pure carboxamides.

Reference： [1]Location in patent: experimental part Chen, Chien-Ting; Hsu, Mei-Hua; Cheng, Yung-Yi; Liu, Chin-Yu; Chou, Li-Chen; Huang, Li-Jiau; Wu, Tian-Shung; Yang, Xiaoming; Lee, Kuo-Hsiung; Kuo, Sheng-Chu [European Journal of Medicinal Chemistry, 2011, vol. 46, # 12, p. 6046 - 6056]

17
[ 41507-35-1 ]
[ 123344-02-5 ]
[ 1417404-04-6 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 241 - 253

18
[ 41507-35-1 ]
[ 78155-75-6 ]
[ 1448314-38-2 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6259 - 6272

19
[ 41507-35-1 ]
[ 78155-74-5 ]
[ 1448314-54-2 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6259 - 6272

20
[ 41507-35-1 ]
[ 1081-04-5 ]
[ 1448314-57-5 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6259 - 6272

21
[ 41507-35-1 ]
[ 93413-62-8 ]
4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenyl thiophene-3-carboxylate [ No CAS ]

Reference： [1]Molecules,2013,vol. 18,p. 14920 - 14934

22
[ 41507-35-1 ]
[ 73540-75-7 ]
[ 32281-36-0 ]

Reference： [1]New Journal of Chemistry,2015,vol. 39,p. 2248 - 2255

23
[ 41507-35-1 ]
[ 19227-14-6 ]
4-bromo-N'-(thiophene-3-carbonyloxy)benzimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With TEA In acetone at 0 - 20℃; for 12h;	Typical proceduresfor the synthesis of O-acylamidoximes1a-w General procedure: b) To a 0 °C mixture of amidoxime (5 mmol) and TEA (5.5 mmol) in acetone (20 mL) was added the acyl chloride (5.5 mmol). The reaction mixture was stirred at room temperature for 12 h. Acetone was evaporated at reduced pressure and to the residue was added water (100 mL). The resulting precipitate was filtered off, washed with water (50 ml) and dried under vacuum at rt.

Reference： [1]Baykov, Sergey; Sharonova, Tatyana; Osipyan, Angelina; Rozhkov, Sergey; Shetnev, Anton; Smirnov, Alexey [Tetrahedron Letters, 2016, vol. 57, # 26, p. 2898 - 2900]

24
[ 41507-35-1 ]
[ 141-78-6 ]
[ 53090-46-3 ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 10405 - 10409

25
[ 41507-35-1 ]
[ 259860-00-9 ]
N-(2-fluoro-4-methyl-5-nitrophenyl)thiophene-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42.7%	Stage #1: 2-fluoro-4-methyl-5-nitro-phenylamine With sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: 3-thiophene carboxylic acid chloride In tetrahydrofuran at 0℃; Inert atmosphere;

Reference： [1]Walter, Niklas M.; Wentsch, Heike K.; Bührmann, Mike; Bauer, Silke M.; Döring, Eva; Mayer-Wrangowski, Svenja; Sievers-Engler, Adrian; Willemsen-Seegers, Nicole; Zaman, Guido; Buijsman, Rogier; Lämmerhofer, Michael; Rauh, Daniel; Laufer, Stefan A. [Journal of Medicinal Chemistry, 2017, vol. 60, # 19, p. 8027 - 8054]

26
[ 22913-26-4 ]
[ 41507-35-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuryl dichloride; sodium hydroxide; In tetrahydrofuran; water; at 20 - 60℃;	<strong>[22913-26-4]Methyl 3-thienylcarboxylate</strong> (1.42 g, 10 mmol) was dissolved in 30 mL THF.An aqueous solution (10 ml) of NaOH (0.8 g, 20 mmol) was added at room temperature.The reaction was stirred at 60 C.TLC testing,After the reaction was completed, it was cooled to room temperature and made acidic with 2M hydrochloric acid.Extracted with ethyl acetate (3 x 30 ml),After the organic phase is combined,Water separately,Saturated saline solution,Dry over anhydrous sodium sulfate.Rotating to remove the solvent,To obtain a crude product of 3-thienylcarbonyl chloride,Can be used directly in the next step.

Reference： [1]Patent: CN108383775,2018,A .Location in patent: Paragraph 0356; 0358-0361

27
[ 41507-35-1 ]
[ 27757-86-4 ]

Reference： [1]MedChemComm,2019,vol. 10,p. 89 - 100

28
[ 41507-35-1 ]
[ 1584139-24-1 ]
C₁₂H₁₆O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine In dichloromethane at 0 - 20℃; for 10h; Schlenk technique; Inert atmosphere;

Reference： [1]Aggarwal, Varinder K.; Madhavachary, Rudrakshula; Noble, Adam; Shu, Chao [Organic Letters, 2020, vol. 22, # 18, p. 7213 - 7218]

29
[ 41507-35-1 ]
[ 60835-71-4 ]
4'-(N-3-thiophenecarboxamido)benzo-15-crown-5 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With triethylamine In dichloromethane at 23℃; for 12h;	2.1. Synthesis 4 -( N -3-thiophenecarboxamido)benzo-15-crown-5 (TH3CA4AB15C5) ( Fig. 1 A), used as a monomer for electro- chemical polymerization, was synthesized at the Department of Organic Chemistry, UCT Prague via the following procedure: Dichloromethane (5 mL) and triethylamine (0.28 mL, 2.0 mmol) were added to a mixture of thiophene-3-carbonyl chloride (176 mg, 1.20 mmol) and 4 -aminobenzo-15-crown-5 ( 283 mg, 1.0 mmol). The resultant mixture was stirred at 23 °C for 12 h. Then the reaction mixture was diluted with dichloromethane (50 mL) and the organic layer was washed with Milli-Q water (2 ×30 mL). The organic layer was dried over MgSO 4 , the solvent was removed under reduced pressure, and column chromatography (silica gel, CHCl 3 /MeOH 9:1, R f 0.15)gave250 mg(64%)oftheamide1 as a white solid, mp = 160.9 -163.9 °C. 1 H NMR ( 400 MHz, CDCl 3 ) δ 8.16 (br s, 1H), 7.97 -7.96 (m, 1H), 7.48 -7.46 (m, 1H), 7.38 (s, 1H), 7.32 -7.30 (m, 1H), 6.98 -6.95 (m, 1H), 6.77 -6.75 (m, 1H), 4.09 -4.03 (m, 4H), 3.88 -3.81 (m, 4H), 3.74 -3.72 (m, 8H). 13 C NMR ( 101 MHz, CDCl 3 ) δ 161.3, 149.3, 145.9, 137.7, 132.0, 128.7, 126.7, 126.3, 114.7, 113.0, 107.5, 77.1, 71.0, 71.0, 70.6, 70.4, 69.7, 69.6, 69.4, 68.7. HRMS (APCI) m/z : [ M + H ] + calcd for C 19 H 23 NO 6 S, 394.1319; found, 394.1323. The data on structure confirmation of newly synthesized compound are in “Supplementary materials ”.

Reference： [1]Shishkanova, Tatiana V.; Štěpánková, Natálie; Tlustý, Martin; Tobrman, Tomáš; Jurásek, Bronislav; Kuchař, Martin; Trchová, Miroslava; Fitl, Přemysl; Vrňata, Martin [Electrochimica Acta, 2021, vol. 373]

30
[ 41507-35-1 ]
[ 4101-30-8 ]
N-(2-acetyl-4,5-dimethoxyphenyl)thiophene-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine In tetrahydrofuran at 0 - 20℃;	4.1.3. General procedure for synthesis of the benzoyl derivatives(11a, b) General procedure: Compound 9 (0.976 g, 5 mmol) was dissolved in dry THF (8 mL)and Et3N (2 mL) and the mixture was cooled in ice bath. Then, a solution of the appropriate benzoyl chloride 10a, b (5.1 mmol) indry THF (2 mL) was added dropwise. After 30 min at 0 C, the reactionmixture was stirred overnight at room temperature. Afterreaction completion, the reaction mixture was poured into icewater (50 mL). The precipitate separated was filtered off, washedseveral times with water then methanol, dried under vacuum andcrystallized from acetone to afford compounds 11a, b as yellowcrystals.

Reference： [1]Elbadawi, Mostafa M.; Eldehna, Wagdy M.; Wang, Wenjie; Agama, Keli K.; Pommier, Yves; Abe, Manabu [European Journal of Medicinal Chemistry, 2021, vol. 215]

31
[ 41507-35-1 ]
[ 75-04-7 ]
[ 150079-41-7 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; water monomer at 20℃; for 6h; Sealed tube; Inert atmosphere;

Reference： [1]Li, Jingya; Li, Zhongxian; Mu, Bing; Wang, Zechao; Wu, Junliang; Wu, Linna; Xia, Shiwei [Journal of Organic Chemistry, 2022, vol. 87, # 7, p. 4918 - 4925]

CAS No. :	41507-35-1	MDL No. :	MFCD00130090
Formula :	C₅H₃ClOS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QTWBEVAYYDZLQL-UHFFFAOYSA-N
M.W :	146.59	Pubchem ID :	2776377
Synonyms :

Signal Word:	Danger	Class:	8,4.1
Precautionary Statements:	P210-P240-P241-P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P370+P378-P405-P501	UN#:	2921
Hazard Statements:	H228-H314	Packing Group:	Ⅱ
GHS Pictogram:

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H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 41507-35-1 ] {[proInfo.proName]}

Quality Control of [ 41507-35-1 ]

Related Doc. of [ 41507-35-1 ]

Product Details of [ 41507-35-1 ]

Safety of [ 41507-35-1 ]

Application In Synthesis of [ 41507-35-1 ]

[ 41507-35-1 ] Synthesis Path-Upstream 1~8

[ 41507-35-1 ] Synthesis Path-Downstream 1~31

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry