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Chemical Structure| 938-73-8 Chemical Structure| 938-73-8
Chemical Structure| 938-73-8

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2-Ethoxybenzamide is an anti-inflammatory drug used for the relief of fever, headaches, and other minor aches and pains.

Synonyms: Ethenzamide

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Product Details of 2-Ethoxybenzamide

CAS No. :938-73-8
Formula : C9H11NO2
M.W : 165.19
SMILES Code : O=C(N)C1=CC=CC=C1OCC
Synonyms :
Ethenzamide
MDL No. :MFCD00007977
InChI Key :SBNKFTQSBPKMBZ-UHFFFAOYSA-N
Pubchem ID :3282

Safety of 2-Ethoxybenzamide

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of 2-Ethoxybenzamide

* 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 [ 938-73-8 ]

[ 938-73-8 ] Synthesis Path-Downstream   1~5

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  • [ 134-11-2 ]
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YieldReaction ConditionsOperation in experiment
90% With thionyl chloride; In 5,5-dimethyl-1,3-cyclohexadiene; 4.2 2-Ethoxybenzamidine hydrochloride 6 2-Ethoxybenzonitrile was prepared from 2-ethoxybenzamide 5 according to the method reported by Nowakowski 23 in 89% yield (lit. 23 yield 92%); Rf (hexane/EtOAc 9:1) 0.45; numax (crystal): 2231 cm-1 (C?N). 1H NMR (CDCl3, delta ppm): 7.57-7.51 (m, 2H, 4-H and 5-H of C6H4), 7.01 (d, J 7.3 Hz, 1H, 6-H of C6H4), 6.97 (d, J 8.8 Hz, 1H, 3-H of C6H4), 4.17 (q, J 7 Hz, 2H, OCH2), 1.49 (t, J 7.1 Hz, 3H, CH3). Ethyl 2-ethoxybenzimidate hydrochloride was synthesized by passing dry HCl(gas) through the solution of 2-ethoxybenzonitrile in anhydrous ethyl alcohol. This compound was obtained as a white solid (46%); mp 49-54 C; Rf (hexane/EtOAc 7:3) 0.36. 1H NMR (CDCl3, delta ppm): 13.01 (br s, 1H, NH), 10.14 (br s, 1H, NH), 8.04 (dd, J 1.7 and 8 Hz, 1H, 6-H of C6H4), 7.74-7.70 (m, 1H, 4-H of C6H4), 7.18-7.14 (m, 2H, 3-H and 5-H of C6H4), 5.04 (q, J 7 Hz, 2H, NCOCH2), 4.39 (q, J 7 Hz, 2H, OCOCH2), 1.63 (t, J 7.1 Hz, 3H, NCOCH2CH3), 1.57 (t, J 6.8 Hz, 3H, OCOCH2CH3).
90% General procedure: BrCCl3 (900 mg, 4.6 mmol) was added to PPh3 (1.22 g, 4.6 mmol) in dry CH2Cl2 (12 mL) and the resulting mixture was stirred at room temperature for 20 min, during which time the solution turned from yellow to red-brownish in colour.Thereafter, 3-chlorobenzamide (1i, 500 mg, 3.2 mmol) was added. Thereaction mixture was heated under reflux for 25 min. Then, dry Et3N (465 mg, 4.6 mmol) was added dropwise with a syringe over 1 min.The reaction mixture was heated under reflux for 12 h. Thereafter,it was cooled to room temperature and added to cold water (50 mL).The mixture was extracted with dichloromethane (2 × 30 mL) and chloroform (30 mL). The combined organic phases were dried over anhydrous MgSO4, concentrated under reduced pressure and subjected to column chromatography on silica gel (CH2Cl2/hexane 4 : 1) to give 3-chlorobenzonitrile (2i, 320 mg, 72%) as a colourless solid.
With thionyl chloride; In toluene; Ib) Preparation of 2-ethoxybenzonitrile 260 kg of thionyl chloride are added at 85-95 C. to a suspension of 250 kg of 2-ethoxybenzamide in toluene under metering control. The reaction mixture is stirred in the presence of heat. Thionyl chloride and toluene are then distilled off in vacuo. The product is employed in the subsequent stage as a crude product. Yield: 228.5 kg (crude product) 1H-NMR: delta=1.45 (t, 3H), 4.15 (q, 2H), 7.0 (m, 2H, phenyl), 7.5 (m, 2H, phenyl) MS: 312 (2M+NH4, 35), 165 (M+NH4, 100), 147 (5)
  • 4
  • [ 6609-57-0 ]
  • [ 938-73-8 ]
YieldReaction ConditionsOperation in experiment
98% With [2,2]bipyridinyl; water; palladium diacetate; In 1,4-dioxane; at 90℃; for 24h;Schlenk technique; Sealed tube; General procedure: To an oven dried Schlenk carousel tube containing the appropriate nitrile (1 mmol) was added palladium acetate (11 mg, 5 mol%), 2,2'-bipyridine (7.8 mg, 5 mol%), dioxane (0.6 mL) and water (1.4 mL). The tube was then sealed and the reaction mixture heated at 70 C (unless otherwise stated) for 24 hours. After being allowed to cool to room temperature, the reaction mixture was diluted with methanol (5 mL) and the solvent removed in vacuo on a rotary evaporator whilst azeotroping with toluene. Where the reaction had gone to quantitative conversion or the starting nitrile was volatile, the crude reaction mixture was passed through a short plug of silica to remove the catalyst (eluting with DCM/MeOH, 95:5). Otherwise, the primary amide products were purified by column chromatography (eluting with DCM/MeOH, 95:5, unless otherwise stated).
19.7 g With potassium tert-butylate; In toluene; at 60℃;Inert atmosphere; Under nitrogen protection,200 mL of ethanol, cuprous iodide (3.8 g, 0.02 mol) and potassium hydroxide (16.8 g, 0.3 mol) were mixed uniformly,O-chlorobenzonitrile (27.5 g, 0.2 mol) was added,And then heated to 80 insulation reaction,TLC or liquid phase monitoring reaction,After completion of the reaction, ethanol was recovered,Down to room temperature,Add 100 mL of water and 150 ml of toluene to wash with water,And then toluene recovery,The intermediate of o-ethoxybenzene was purified by distillation under reduced pressure (23.5 g (154 C / 20 Torr).20.6 g (0.14 mol) of <strong>[6609-57-0]o-ethoxybenzonitrile</strong> was dissolved in 150 mL of toluene, potassium tert-butoxide (47.1 g,0.42 mol), heated to 60 C to carry out the reaction, TLC or liquid phase monitoring reaction, the reaction is completed by adding 150mL of water for washing,The organic phase recovered the solvent and the residue was recrystallized from ethanol and dried to give 19.7 g of 2-ethoxybenzamide as a white solid.
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YieldReaction ConditionsOperation in experiment
4.46 g With ammonium hydroxide; In chloroform; at -10℃; Benzo[d][1,3]dioxole-5-carboxylic acid (8.00 g, 48.1 mmol), SOCl2 (10.4 mL, 144 mmol) and DMF (0.15 mL, 2 mmol) were mixed together in a flask protected with CaCl2 trap and stirred magnetically at r.t. After 24 h, the homogeneous mixture was diluted with toluene (100 mL) and concentrated on a rotary evaporator at 40 C; the residue was diluted with CHCl3 (20 mL) at -10 C and added dropwise to stirred aqueous ammonia (25%, 30 mL) at -10 C. The layers were separated, the aqueous layer was extracted with CHCl3 (2 × 25 mL) and the combined organic extracts were concentrated on a rotary evaporator at 20-80 C. The residue was used without further purification.
 

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