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CAS No. :14949-01-0 MDL No. :MFCD00034074
Formula : C8H9ClN2O3S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 248.69 Pubchem ID :-
Synonyms :

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* 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 [ 14949-01-0 ]

[ 14949-01-0 ] Synthesis Path-Downstream   1~21

  • 2
  • [ 30090-17-6 ]
  • [ 14949-01-0 ]
  • [ 76663-03-1 ]
  • 3
  • [ 14949-01-0 ]
  • [ 2696-84-6 ]
  • [ 76662-97-0 ]
  • 4
  • [ 14949-01-0 ]
  • [ 93-50-5 ]
  • 2-(4-Chloro-2-methoxy-phenylamino)-N-(4-sulfamoyl-phenyl)-acetamide [ No CAS ]
  • 5
  • [ 14949-01-0 ]
  • [ 2909-84-4 ]
  • [ 76663-08-6 ]
  • 6
  • [ 14949-01-0 ]
  • [ 33311-29-4 ]
  • [ 76663-16-6 ]
  • 7
  • [ 63-74-1 ]
  • [ 79-04-9 ]
  • [ 14949-01-0 ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate In tetrahydrofuran at 0℃;
95% With potassium carbonate In acetone at 0 - 20℃; 4.1.3. Synthesis of 2-chloro-N-(4-sulfamoylphenyl)-acetamide716 To a solution of sulfanilamide 5 (1.72 gm, 0.01 mol) and K2CO3 (2.76 g, 0.02 mol) in acetone (20 mL), 2-chloroacetyl chloride 6(1.354 g, 0.012 mol) was added drop-wise. The reaction mixturewas stirred at 0 C for 0.5 h then left to warm to room temperature.The progress of the reaction was monitored by TLC till completion.The reaction mixture was filtered and the filtrate was evaporatedunder reduced pressure to afford the crude product, which waswashed with water and crystallized from ethanol to afford analyticallypure product of compound 7.
89% In acetone at 20 - 95℃; for 1h; 2 PREPARATION 2 PREPARATION OF 2-CHLORO-/V- 4-SULFAMOYLPHENYL)ACETAMIDE PREPARATION 2 PREPARATION OF 2-CHLORO-/V- 4-SULFAMOYLPHENYL)ACETAMIDE Sulfanilamide (10.0 g, 58.1 mmol) was suspended in acetone (30 mL), chloroacetyl chloride (4.49 mL, 55.3 mmol) was added drop-wise at ambient temperature. The reaction mixture was stirred at 95 °C for 1 hour and then cooled to ambient temperature. Ice-water was added and the resulting mixture was stirred for a while and filtered. The solid collected was washed with ice-water and re-crystallized from ethanol. The solid was collected by filtration and dried in vacuo to afford the title compound as a white solid (8.84 g) and the filtrate was concentrated to yield more product (3.42 g). The total yield was 89%. 1 H N MR (300 MHz, DMSO-d6): 5 10.61 (s, 1 H), 7.81 -7.71 (m, 4H), 7.26 (br s, 2H), 4.29 (s, 2H).
89% In acetone at 95℃; for 1h;
88% With potassium carbonate In acetone at 20℃;
88% With potassium carbonate In acetone at 0 - 20℃; Inert atmosphere; 4.2.2. General procedure for synthesis of 2-chloro-(4-sulfamoylphenyl)acetamide (4) To a solution of Sulfanilamide 3 (1 equiv) and K2CO3 (2 equiv) in 20ml acetone, 2-chloroacetylchloride (2 equiv) was added drop-wise. The reaction mixture was stirred at 0 0C for 1h and then left to warm at room temperature. After completion of reaction filter and dry it washed with ethanol yields 88%.
87% With triethylamine In dichloromethane at 50℃; for 4h;
84% With potassium carbonate In tetrahydrofuran at 0℃; for 0.5h;
80% In 1,4-dioxane; benzene for 1h;
78.2% With potassium carbonate In acetone at 0 - 15℃;
75% With potassium carbonate In acetone at 0℃;
37% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; 4.2.8. General procedures for the synthesis of 2-chloro-N-phenylacetamides(5-19) General procedure: The desired compounds (5-19) were obtained following aprocedure previously reported by us.21Particularly, chloroacetyl chloride (78 ll, 1 mmol) and N,Ndiisopropylethylamine(175 ll, 1 mmol) were added dropwise to a solution of the appropriate substituted anilines in DCM (5 mL).The mixture was stirred for 1 h at room temperature. Successively,the reaction was quenched with a saturated NaHCO3 aqueous solution(5 mL). The reaction mixture was extracted with EtOAc (3 10 mL), dried over Na2SO4 and evaporated under reduced pressure.The residue was crystallized from EtOH or Et2O.
21% With triethylamine In acetone at 20℃; Cooling with ice; 3.1.2. Preparation of the Mono-chloromethyl-acetamido-Derivatives (7-12) General procedure: Mono-chloromethyl-acetamido- derivatives were preparedas described earlier [24]. Briefly: To a magneticallystirred, ice-bathed, solution or suspension of the particularcommercially available sulfanilamide or aniline (1.0 equivalent)and triethylamine (2.0 equivalents) in dry acetone (25ml), chloroacetylchloride (1.5 equivalents) in dry acetone (25ml) was gradually added over 30 minutes. The reaction mixturewas stirred at room temperature until TLC revealedcomplete consumption of the starting amine. Subsequently,the reaction mixture was poured slowly onto ice water (100ml). The precipitated crude products were purified by recrystallizationfrom acetone/water. Scheme 1 shows the preparedcompounds and their corresponding starting materials.
With N-ethylmorpholine; In tetrahydrofuran at -15℃;
In water monomer 1.a a. a. α-Chloro-4-sulphamoylacetanilide Sulphanilamide (17.2g) and α-chloroacetyl chloride (7.55 ml) were refluxed together for 1 hour, cooled, ground in a mortar with ice/water and filtered to give 26.5 g of the title compound. Recrystallisation from ethanol gave m.p. 215°-219°. C8 H9 CIN2 O3 S (248.69) Requires: C, 38.64; H, 3.64; N, 11.26%. Found: C, 38.57; H, 3.65; N, 11.30%.
With potassium carbonate In tetrahydrofuran Reflux;
With N-Ethylmaleimide In tetrahydrofuran Inert atmosphere;
In N,N-dimethyl-formamide
With triethylamine In dichloromethane at 0℃; for 5h;
In N,N-dimethyl-formamide at 20℃;
In N,N-dimethyl-formamide
In 1,4-dioxane at 0 - 20℃; for 2.5h; 4.1.1 Synthesis of compounds (7a-e) General procedure: To a stirred solution of the appropriate sulfa drugs 1a-c (100 mmol) in dioxan (20 mL), 2-chloroacetyl chloride (6a) (0.113 g, 100 mmol) or 3-chloropropanoyl chloride (6b) (0.127 g, 100 mmol) was added drop wise at 0 °C during 30 min, and stirring continued for 2 h at room temperature. The obtained precipitate was filtered, dried and recrystallized from ethanol to yield 7a-e. The physical properties and spectral data of 7a-d were identical to those reported [28-31].
With triethylamine In dichloromethane for 1h; 1 2-Chloroacetyl chloride (1.12 g, 0.01 mol) (2) was added dropwise with vigorous stirring to a cold suspension of sulfanilamide (1.72 g, 0.01 mol) (1) in 10 ml dichloromethane containing 2 drops triethylamine. Stirring was continued for 1 hour and the separated solid was filtered, washed with ether, dried and crystallized from aqueous-ethanol. [0025] Yield, 69%; M.P. 270-272° C.; 1H NMR (DMSOd6): δ 0.90 (d, 6H, J=12.0 Hz, 2CH3), 1.49 (m, 1H, CH), 1.80 (t, 2H, J=9.0 Hz, CH2), 2.51 (s, 1H, NH, D2O exchange.), 3.26 (s, 2H, CH2), 3.49 (t, 1H, J=8.5 Hz, CH), 4.21 (s, 2H, NH2, D2O exchange.), 7.30 (s, 1H, NH, D2O exchange.), 7.60 (d, 2H, J=7.5 Hz, Ar-H), 7.79 (d, 2H, J=7.67 Hz, Ar-H), 10.55 (s, 1H, OH, D2O exchange). 13C NMR: δ 22.6 (2CH3), 24.3 (CH), 41.1 (CH2), 50.2 (CH2), 59.4 (CH), 118.6, 126.7, 138.4, 141.4 (Ar-C), 169.0, 174.7 (2C=O). MS (EI): m/z 343 [M+, %]. Anal. (C14H21N3O5S) C, H, N. [0026] The obtained alkyl halide (3) was then refluxed with leucine (4) in alcohol containing anhydrous potassium carbonate in the presence of catalytic amount of potassium iodide. The product ( 5) was obtained in about 50% yield and purified by column chromatography. The structure was confirmed by NMR spectra. The spectrum showed the aliphatic protons at δ of 0.9 ppm, two different protons on two different tertiary carbons δ at 1.49 and 3.49 and the carbons bearing them at 22.6, 24.3 and 59.9 respectively. Two CH2 groups at δ 1.80, 3.26 and their carbons appeared at 41.1, 50.2, respectively. The SO2NH2 protons were found at δ 4.21. Two singlets corresponding to two NH groups were seen at δ 2.51 and 7.30, respectively. One OH appeared at δ 10.55 due to the free carboxyl group of leucine. The two carbonyl groups were seen at δ 169.0 and 174.7. The two dimensional spectrum showed that the obtained structure is in accordance with the proposed one.
In N,N-dimethyl-formamide at 20℃;
With potassium carbonate In tetrahydrofuran for 0.75h; Inert atmosphere; Cooling with ice;
In N,N-dimethyl-formamide at 20℃; for 2h;
With triethylamine In dichloromethane Reflux;
With triethylamine In dichloromethane for 1h; Cooling; 1 Synthesis of 2-Chloro-N-(4-aminosulphonylphenyl)acetamide (Compound 1) 2-Chloroacetyl chloride (1.12 g, 0.01 mole) was added drop wise with vigorous stirring to a cold suspension of sulfanilamide (1.72 g, 0.01 mole) in 10 ml dichloromethane containing 2 drops triethylamine. Stirring was continued for 1 hour and the separated solid was filtered, washed with ether, dried and crystallized from aqueous-ethanol.
In N,N-dimethyl-formamide at 0 - 20℃; for 2h; 4.1.2. General procedure for preparation of 2-chloro-N-(4/3-sulfamoylphenyl)acetamides 2a, b General procedure: To a solution of sulfanilamides 1a, b (1.72 gm, 10 mmol) in dryDMF, chloroacetyl chloride (0.8 mL, 10 mmol) was added dropwiseat 0 °C then stirred at room temperature for 2 h. The reactionmixture was then poured into ice-water. The obtained solid was filtered off, washed with water several times and crystallized fromdioxane to give compounds 2a, b
With potassium carbonate In N,N-dimethyl-formamide
With N,N-dimethyl-formamide at 20℃;
In N,N-dimethyl-formamide at 20℃;
With triethylamine In N,N-dimethyl-formamide at 20℃; General procedure of synthesis of Intermediate (2a-2f) General procedure: To a stirred solution of sulphonamide (2 mmol) in dimethylformamideat 0-5 °C, chloro acetyl chloride (6 ml) wasadded dropwise and stirred at room temperature for 3-4 hoursby a magnetic stirrer. The reaction mixture was neutralizedwith triethylamine then the precipitate was filtered, washedwith cold water recrystallized from methanol
With triethylamine In tetrahydrofuran at 0 - 5℃; for 0.75h; 2.2 2.2. Synthesis of 2-chloro-N-(4-sulfamoylphenyl) acetamide (3) To a stirred solution of 4-aminobenzene sulfonamide (4 mmol) in tetrahydrofuran, at 0-5 °C in ice jacket, 2-chloroacetyl chloride (4.5 mmol) was added drop wise over a 15-min period. The reaction mixture was further stirred for half an hour. On completion of reaction, the white precipitate appeared was filtered, washed and recrystallize with ethanol.
With triethylamine In dichloromethane
With potassium carbonate In N,N-dimethyl-formamide
In N,N-dimethyl-formamide at 0℃; for 1h; 2.1.1 2-Chloro-N-(4-sulfamoylphenyl)acetamide (1) Chloroacetyl chloride (2.16mL, 27.8mmol) was added dropwise with stirring to a solution of 4-aminobenzenesulfonamide (4g, 23.2mmol) in DMF (20mL). After the completion of dropping, the mixture was stirred for 1h and then poured into the iced-water (100mL). Precipitated product was filtered, washed with water, dried, and recrystallized from ethanol.
In N,N-dimethyl-formamide at 20℃; for 1h; Cooling with ice; 4.1.1. General procedure for the synthesis of the compounds 4.1.1.1. Synthesis of 2-chloro-N-(4-sulfamoylphenyl)acetamide (1).For the synthesis of the 2-chloro-N-(4-sulfamoylphenyl)acetamide,4-aminobenzenesulfonamide (0.06 mol, 10.1 gr) were dissolved indimethylformamide (20 mL). The mixturewas cooled in an ice bathand chloroacetyl chloride (0.07 mol, 5.8 mL) was added dropwisewith stirring. Then, the reaction mixture was stirred for 1h at room temperature. The reaction content was poured into iced-water andthe precipitated product was washed with water, filtered, dried,and then recrystallized from EtOH.
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 24h; 4.1.2. General procedure to synthesize 2-chloro-N-arylacetamides (7-8) General procedure: The 2-chloro-N-arylacetamide derivatives 7-8 were synthesizedfollowing a previously reported procedure27 introducing slow modificationsas reported below. To a suspension of appropriate aniline(9-10) (1 mmol) in DCM (2 mL) were added dropwise EDIPA (1 mmol,174 μl) and chloroacetyl chloride (1 mmol, 80 μl). The reaction mixturewas stirred at 0 °C for 5 min, and subsequently at room temperature for24 h. The completion of the reaction was followed by TLC Cyclohexane/EtOAc 50:50. Afterwards, H2O (5 mL) and a saturated solutionof NaHCO3 (5 mL) were added to quench the reaction. The obtainedwater layer was extracted with EtOAc (3x10 mL), dried over Na2SO4,filtered and evaporated in vacuo. Desired intermediates 7-8 were purifiedby crystallization from Et2O and MeOH. All spectral data of intermediates7-8 were in good agreement with literature.27
With triethylamine In N,N-dimethyl-formamide at 0℃; for 5h;
In N,N-dimethyl-formamide for 1h;
In N,N-dimethyl-formamide for 1.5h;
In N,N-dimethyl-formamide at 20℃; for 0.5h; 4.3. Synthesis of 2-chloro-N-(4-sulfamoylphenyl)acetamide 8 A mixture of 4-aminobenzenesulfonamide 6 (1 mmol) andchloroacetyl chloride 7 (1.2 mmol) in DMF (10 mL) was stirredat room temperature for 30 min. Then, the reaction mixturewas diluted with water, poured into cold water, and theobtained precipitate was filtered off. This precipitates waswashed with water to give pure 2-chloro-N-(4-sulfamoylphenyl)acetamide 8.
With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h;
With potassium carbonate In acetone at 0℃;
3.96 g In N,N-dimethyl-formamide Synthesis of 2-chloro-N-(4-sulfamoylphenyl)acetamide Obtaining a mixture by dissolving a predetermined amount of 4- aminobenzenesulphonamide (I) in a predetermined amount of DMF (Dimethylformamide) (101), Adding chloroacetylchloride (CICOCH2CI) diluted in a predetermined amount of DMF to the mixture in step 101 dropwise in an ice bath, and stirring the resulting reaction ingredients for a predetermined period of time (102), Upon completion of reaction by TLC (Thin Layer Chromatography), quenching the reaction by pouring the reaction ingredients into ice water, filtering the precipitate and crystallizing the same from ethanol, and synthesizing the final product 2-chloro- N-(4-sulfamoylphenyl)acetamide (103), (0021) In step 101 , the amount of 4-aminobenzenesulphonamide is, but not limited to, 0.023 mol, 3.96 g. (0022) In steps 101 and 102, the amount of DMF is, but not limited to, 15 mL. (0023) In step 102, the amount of chloroacetylchloride is, but not limited to, 0.027 mol, 2.15 mL. In step 102, said period of time is, but not limited to, 1 hour.

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[44]Abdel Gawad, Nagwa M.; El Kerdawy, Ahmed M.; George, Riham F.; Georgey, Hanan H.; Mohamed, Abdalla R. [Bioorganic Chemistry, 2021, vol. 107]
[45]AboulMagd, Asmaa M.; Elsaadi, Mohamed T.; Hamed, Ahmed A.; Hamed, Mohamed I. A.; Hassan, Hossam M.; Nemr, Mohamed T. M. [RSC Advances, 2021, vol. 11, # 42, p. 26241 - 26257]
[46]Current Patent Assignee: ANADOLU UNIVERSITY - WO2022/55467, 2022, A1 Location in patent: Page/Page column 3
  • 8
  • [ 14949-01-0 ]
  • [ 51411-04-2 ]
  • [ 205536-87-4 ]
  • 9
  • [ 14949-01-0 ]
  • [ 5536-61-8 ]
  • [ 473989-26-3 ]
  • 10
  • [ 5004-45-5 ]
  • [ 14949-01-0 ]
  • [ 1622427-21-7 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 2-chloro-N-(4-sulfamoylphenyl)acetamide With potassium carbonate In acetone for 1h; Reflux; Stage #2: 4-phenyl-2H-phthalazin-1-one In acetone for 12h; Reflux; Method A General procedure: To a solution of the appropriate amides 7a-e (2 mmol) in acetone (20 mL), K2CO3 (0.69 g, 5 mmol) was added and reflux for 1 h. For this solution, the appropriate phthalazin-1(2H)-ones 9a, b or 14a, b (2mmol) was added and the reflux was continued for 12 h, then left to cool at room temperature and poured into cursed ice. The resulted precipitate was filtered, dried and then recrystallized from DMF/H2O to afford the targeted compounds.
  • 11
  • [ 25475-67-6 ]
  • [ 14949-01-0 ]
  • 2-(isoquinolin-3-ylamino)-N-(4-sulfamoylphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With triethylamine; In N,N-dimethyl-formamide; for 17h;Reflux; General procedure: A mixture of compound 1a (2.489 g, 0.01 mol) and required amines, namely: adamantylamine, 5-aminoindanone, 4-morpholinobenzamine, piperonylamine,2-amino-6-fluorobenzothiazole, 2-amino-6-ethoxybenzothiazole, 2-amino-5,6-dimethyl-benzothiazole,2-amino-1-ethylpyrazole, 2-amino-5-ethylthiadiazole, 2-amino-5-thioethylthiadiazole, 3-aminoquinoline and 2-aminoisoquinoline (0.01 mol) in dimethylformamide (20 mL) containing 3 drops of triethylamine was refluxed for 17 h. The reaction mixture was collected and poured onto ice/water. The obtained solid was recrystallized from dioxane to give derivatives 2-13, respectively.
  • 12
  • [ 29927-08-0 ]
  • [ 14949-01-0 ]
  • 2-(5,6-dimethylbenzo[d]thiazol-2-ylamino)-N-(4-sulfamoylphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With triethylamine; In N,N-dimethyl-formamide; for 17h;Reflux; General procedure: A mixture of compound 1a (2.489 g, 0.01 mol) and required amines, namely: adamantylamine, 5-aminoindanone, 4-morpholinobenzamine, piperonylamine,2-amino-6-fluorobenzothiazole, 2-amino-6-ethoxybenzothiazole, <strong>[29927-08-0]2-amino-5,6-dimethyl-benzothiazole</strong>,2-amino-1-ethylpyrazole, 2-amino-5-ethylthiadiazole, 2-amino-5-thioethylthiadiazole, 3-aminoquinoline and 2-aminoisoquinoline (0.01 mol) in dimethylformamide (20 mL) containing 3 drops of triethylamine was refluxed for 17 h. The reaction mixture was collected and poured onto ice/water. The obtained solid was recrystallized from dioxane to give derivatives 2-13, respectively.
  • 13
  • [ 14949-01-0 ]
  • [ 3528-58-3 ]
  • 2-(1-ethyl-1H-pyrazol-5-ylamino)-N-(4-sulfamoylphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With triethylamine; In N,N-dimethyl-formamide; for 17h;Reflux; General procedure: A mixture of compound 1a (2.489 g, 0.01 mol) and required amines, namely: adamantylamine, 5-aminoindanone, 4-morpholinobenzamine, piperonylamine,2-amino-6-fluorobenzothiazole, 2-amino-6-ethoxybenzothiazole, 2-amino-5,6-dimethyl-benzothiazole,2-amino-1-ethylpyrazole, 2-amino-5-ethylthiadiazole, 2-amino-5-thioethylthiadiazole, 3-aminoquinoline and 2-aminoisoquinoline (0.01 mol) in dimethylformamide (20 mL) containing 3 drops of triethylamine was refluxed for 17 h. The reaction mixture was collected and poured onto ice/water. The obtained solid was recrystallized from dioxane to give derivatives 2-13, respectively.
  • 14
  • [ 14068-53-2 ]
  • [ 14949-01-0 ]
  • 2-(5-ethyl-1,3,4-thiadiazol-2-ylamino)-N-(4-sulfamoylphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With triethylamine In N,N-dimethyl-formamide for 17h; Reflux; General procedure for the synthesis of sulfonamides(2-13) General procedure: A mixture of compound 1a (2.489 g, 0.01 mol) and required amines, namely: adamantylamine, 5-aminoindanone, 4-morpholinobenzamine, piperonylamine,2-amino-6-fluorobenzothiazole, 2-amino-6-ethoxybenzothiazole, 2-amino-5,6-dimethyl-benzothiazole,2-amino-1-ethylpyrazole, 2-amino-5-ethylthiadiazole, 2-amino-5-thioethylthiadiazole, 3-aminoquinoline and 2-aminoisoquinoline (0.01 mol) in dimethylformamide (20 mL) containing 3 drops of triethylamine was refluxed for 17 h. The reaction mixture was collected and poured onto ice/water. The obtained solid was recrystallized from dioxane to give derivatives 2-13, respectively.
  • 15
  • [ 14949-01-0 ]
  • [ 13074-39-0 ]
  • 2-(adamantan-2-ylamino)-N-(4-sulfamoylphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With triethylamine In N,N-dimethyl-formamide for 17h; Reflux; General procedure for the synthesis of sulfonamides(2-13) General procedure: A mixture of compound 1a (2.489 g, 0.01 mol) and required amines, namely: adamantylamine, 5-aminoindanone, 4-morpholinobenzamine, piperonylamine,2-amino-6-fluorobenzothiazole, 2-amino-6-ethoxybenzothiazole, 2-amino-5,6-dimethyl-benzothiazole,2-amino-1-ethylpyrazole, 2-amino-5-ethylthiadiazole, 2-amino-5-thioethylthiadiazole, 3-aminoquinoline and 2-aminoisoquinoline (0.01 mol) in dimethylformamide (20 mL) containing 3 drops of triethylamine was refluxed for 17 h. The reaction mixture was collected and poured onto ice/water. The obtained solid was recrystallized from dioxane to give derivatives 2-13, respectively.
58% With potassium carbonate; potassium iodide In tetrahydrofuran; ethanol Reflux; 2.3. Synthesis of 2-(substituted phenylamino)-N-(4-sulfamoylphenyl)acetamides (4a-4m) General procedure: Suitably substituted aniline (2.016 mmol) were added along with anhydrous potassium carbonate and a catalytic amount of potassium iodide to the stirred solution of 2-chloro-N-(4-sulfamoylphenyl) acetamide (3) (0.5 g, 2.016 mmol) in the mixture of tetrahydrofuran and ethanol (10 mL). The reaction mixture was heated under reflux for 6-7 h. The solid products thus appeared were filtered, washed and recrystallized with ethanol: chloroform (1:1) mixture.
  • 16
  • [ 14949-01-0 ]
  • [ 57-41-0 ]
  • 2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)-N-(4-sulfamoylphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In acetone at 20℃; for 24h; 4 General procedure for the synthesis of compounds 2-10 General procedure: A mixture of 5,5-diphenylimidazolidine-2,4-dione (1) (1.0mmol, 0.252gm), N-aryl-2-chloroacetamide (1.2mmol) and anhydrous potassium carbonate (2.0mmol, 0.276gm) in dry acetone (10mL) was stirred at room temperature for 24h. The reaction mixture was filtered off, the solvent was removed under reduced pressure and the solid obtained was washed with water, dried and re-crystallized from an appropriate solvent.
  • 17
  • [ 5835-46-1 ]
  • [ 14949-01-0 ]
  • C19H17N3O6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 40℃; for 6h; 4 Preparation of (Z)-2-[5-(2-methoxystyryl)-2,4-dicarbonylthiazol-3-yl]-N-4- (sulfamoylphenyl)acetamide (LW-4) 4b (0.2 g, 0.76 mmol) and 4 (0.18 g, 0.76 mmol) were dissolved in 10 mL of THF. It was then added DIPEA (0.2 mL, 1.52 mmol) with stirring. The reaction was heated to 40°C for 6h. It was dried and recrystallized with ethanol. Dried to give a yellow solid 0.14 g, yield 40%.
  • 18
  • [ 14949-01-0 ]
  • [ 59564-59-9 ]
  • 2-(3-oxo-3,4-dihydroquinoxalin-1(2H)-yl)-N-(4-sulfamoylphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.63% With sodium hydrogencarbonate; potassium iodide In N,N-dimethyl-formamide for 20h; Heating; 4.1.3. 2-(3-Oxo-3,4-dihydroquinoxalin-1(2H)-yl)-N-(4-sulfamoylphenyl)acetamide (18) A mixture of 3,4-dihydroquinoxalin-2(1H)-one 17 (2.98 g,20.11 mmol), 2-chloro-N-(4-sulfamoylphenyl)acetamide 13(5.00 g, 20.11 mmol), NaHCO3 (1.69 g, 20.11 mmol) and KI(0.10 g, 0.60 mmol, catalytic amount) in DMF (30 ml) was heatedon a water bath for 20 h. After cooling, the reaction mixture pouredonto crushed ice. The formed precipitate was collected by filtration,dried, washed by boiled absolute ethanol and filtered to givecompound 18.Yellow powder (yield 72.63); m.p. 250-253 C; IR (KBr, t cm1):3382, 3268 (NH2 & 2NH, overlapped), 3121 (CAH Aromatic), 1668(CO amide), 1599 (CN quinoxaline), 1531 (amide II band), 1307,1148 (SO2); 1H NMR (DMSO-d6, 600 MHz) d (ppm): 4.02 (s, 2H,COCH2), 4.15 (s, 2H, CH2 quinoxaline), 7.27 (s, 2H, D2O exchangeable,NH2), 6.57 (d, J = 7.8 Hz, 1H, ArAH quinoxaline), 6.68 (dd,J = 7.8, 7.2 Hz, 1H, ArAH quinoxaline), 6.83 (d, J = 7.2 Hz, 2H, ArAHphenyl), 7.77-7.80 (m, 4H, ArAH), 10.44 (s, 1H, D2O exchangeable,NH amide), 10.50 (s, 1H, D2O exchangeable, NH quinoxaline); 13CNMR (DMSO-d6, 150 MHz) d (ppm): 52.81, 53.59, 111.69, 115.51,118.97, 119.32, 123.47, 127.19, 127.32, 135.18, 138.91, 142.09,166.08, 168.92; DEPT spectrum showed two CH2 and six differentCH; MS (m/z): 361 (M++1, 1.33%), 360 (M+, 7.00%), 281 (15.62%),214 (8.65%), 187 (48.01%), 172 (80.10%), 162 (13.30%), 161 (100%,base peak), 156 (64.42%), 147 (30.00%), 133 (70.70%), 119(38.62%), 92 (76.40%), 77 (21.77%), 58 (15.59%); Anal. Calcd. forC16H16N4O4S (360.39): C, 53.32; H, 4.48; N, 15.55; S, 8.90; Found:C, 53.51; H, 4.51; N, 15.78; S, 8.94.
  • 19
  • [ 1769-24-0 ]
  • [ 14949-01-0 ]
  • 2-methyl quinazolin-4-one [ No CAS ]
  • 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(4-sulfamoylpheyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 2-methyl-4-quinazolone With potassium hydroxide Stage #2: 2-chloro-N-(4-sulfamoylphenyl)acetamide; 2-methyl quinazolin-4-one With potassium iodide In N,N-dimethyl-formamide for 12h; Reflux; 1 General procedure for synthesis of compounds (24a-c) General procedure: A mixture of potassium salt of 2-methyl-quinazolin-4(3H)-one23a, (9.91 g, 0.05 mol), potassium salt of 2-ethyl-quinazolin-4(3H)-one 23b, (10.61 g, 0.05 mol) or 6-bromo-2-methylquinazolin-4(3H)-one 23c, (13.85 g, 0.05 mol) and 2-chloro-N-(4-sulfamoylphenyl)acetamide 17 (12.4 g, 0.05 mol) in dry DMF(50 mL) was heated over a water bath for 12 h. After cooling to room temperature, the reaction mixture was poured on ice-cold water (500 mL). The formed white precipitated product was filtered,washed with water and hot ethanol to afford compounds 24a-c, respectively.
  • 20
  • [ 14949-01-0 ]
  • [ 146381-56-8 ]
  • 2-((3-cyclopropyl-4-oxo-3,4-dihydroquinazolin-2-yl)thio)-N-(4-sulfamoylphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h; 4.4. General procedure for the synthesis ofquinazolin-sulfonamid derivatives 9a-m General procedure: A mixture of 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives5a-m (1 mmol), 2-chloro-N-(4-sulfamoylphenyl)acetamide8 (1 mmol) and, potassium carbonate (2 mmol) in DMF(10 ml) was heated at 60 C for 4 h. Thereafter, the mixturereaction was poured in cold water and the residue was filtratedand purified using recrystallization from ethanol togive quinazolin-sulfonamid derivatives 9a-m.
  • 21
  • [ 14949-01-0 ]
  • [ 27386-01-2 ]
  • C11H12N4O3S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetone at 20℃; Synthesis _ of _ 2-((5-(substitutedamino)-1 ,3,4-thiadiazole-2-yl)thio)-N-(4- sulfamoylphenvDacetamide (4a-4k) A method (100) for synthesizing 4-(2-((5-(substitutedamino)-1 ,3,4-thiadiazole-2- yl)thio)acetyl)benzenesulphonamide according to the following steps: Mixing a predetermined amount of 5-(substitutedamino)-1 ,3,4-thiadiazole-2-thiol (3a- 3k) and 2-chloro-N-(4-sulfamoylphenyl)acetamide (1) in acetone in the presence of potassium carbonate as a catalyst at room temperature for a predetermined period of time (111), Upon completion of reaction by TLC, removing acetone using a rotavapor, obtaining the product by washing the medium with water, drying the product and crystallizing it from ethanol (112). (0033) In step 111 , the amount of 5-(substitutedamino)-1 ,3,4-thiadiazole-2-thiol is, but not limited to, 4.1 moles. (0034) In step 111 , the amount of 2-chloro-N-(4-sulfamoylphenyl)acetamide is, bit not limited to, 0.53 g, 4.1 mmol. (0035) In step 111 , the amount of acetone is, but not limited to, 30 mL. (0036) In step 111 , said period of time is, but not limited to, 3 hours.
Same Skeleton Products
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