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Chemical Structure| 1121-89-7 Chemical Structure| 1121-89-7
Chemical Structure| 1121-89-7

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Product Details of Glutarimide

CAS No. :1121-89-7
Formula : C5H7NO2
M.W : 113.11
SMILES Code : O=C(CCC1)NC1=O
MDL No. :MFCD00006670
InChI Key :KNCYXPMJDCCGSJ-UHFFFAOYSA-N
Pubchem ID :70726

Safety of Glutarimide

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P305+P351+P338

Application In Synthesis of Glutarimide

* 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 [ 1121-89-7 ]

[ 1121-89-7 ] Synthesis Path-Downstream   1~9

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YieldReaction ConditionsOperation in experiment
65% Into a stirred solution of glutarimide (15.00 g, 0.13 mol) in CH2Cl2 (100 mL) at -78 C under a nitrogen atmosphere, the Grignard reagent CH3MgBr was added into 2-methyltetrahydrofuran (3 M, 130 mL) dropwise. Then the reaction mixture was stirred at room temperature for 12 h. NaBH3CN (9.83 g, 0.16 mol) was added, followed by the slow addition of a 6N HCl solution to keep the pH at 3-4. The reaction was continued at 25 C for 5 h. After completion, the mixture was neutralized with 1 NNaOH and extracted with CH2Cl2 (5 × 100 mL). The combined organic extracts were driedover anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified bycolumn chromatography on silica gel using ethyl acetate:MeOH (20:1~10:1) to obtain compound 3 as a white solid (9.75 g, yield 65%) [45,46]. 1H NMR (400 MHz, CDCl3): δ 1.20(d, 3H, CH3), 1.30-1.37 (m, 1H), 1.66-1.74 (m, 1H), 1.87-1.91 (m, 2H), 2.24-2.31 (m, 1H),2.35-2.41 (m, 1H), 3.48-3.54 (m, 1H), 5.96 (s, br, 1H).
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YieldReaction ConditionsOperation in experiment
82%; 80% With aluminum (III) chloride; at 300℃; for 0.166667h;Microwave irradiation; General procedure: Microwaves Procedure: [0077] The dinitrile (3.0 mmol, 1.0 equiv.) is added, in a glass tube designed for this purpose, to a mixture of acid (3.0 mmol) and catalyst (0.06 mmol, 0.02 equiv.). The tube is then closed using a suitable stopper and then is left under microwave activation (appliance used: Monowave 300 from Anton Paar) and magnetic stirring at 300 C. for 10 min. After reaction, the crude reaction mixture is transferred into a 50 ml round-bottomed flask with 10 ml of ethanol. If necessary, the tube is placed in an ultrasonic bath at 60 C., in order to promote the dissolution of the reaction mixture in the ethanol. 3 g of silica are subsequently added to this mixture in order to produce a solid deposit after evaporation of the ethanol. Finally, the pure nitrile is obtained after chromatography on a silica column (gradient from M1 to M9, followed by M0). For its part, the cyclic imide is obtained after elution with ethyl acetate. The conversion to the desired nitrile is determined by 1H NMR of the crude product. The yields shown are the yields of the isolated products after purification. Note: [0078] M0 is an 80:20 dichloromethane/ethyl acetate mixture. [0079] M1 is a 90:10 petroleum ether/M0 mixture. [0080] M2 is an 80:20 petroleum ether/M0 mixture, and the like. [0081] M9 is a 10:90 petroleum ether/M0 mixture
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YieldReaction ConditionsOperation in experiment
78% With aluminum (III) chloride; at 200℃; for 5h;Sealed tube; General procedure: In a glass tube, the glutaronitrile (282 mg, 3.0 mmol, 1.0 equiv) wasadded to a mixture ofthe respective acid 1(3.0 mmol) and AlCl3(8mg, 0.06 mmol, 0.02 equiv). The tubewas then sealed (with a screwcap) and the mixture was allowed to stir at 200 C for 5 h. Aftercompletion of the reaction, the crude mixture was diluted withEtOH (10 mL), silica gel (3 g) was then added to this crude materialto make a solid deposit after evaporation of the EtOH. A silica gelcolumn chromatography (eluent: PE-EtOAc, 95:5) finally affordedthe pure nitrile together with the cyclic imide. Conversion into thedesired nitrile was determined by 1H NMR analysis of the crudemixture. Given yields were reported for isolated products (Table 2).
 

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