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Chemical Structure| 5332-73-0 Chemical Structure| 5332-73-0

Structure of 5332-73-0

Chemical Structure| 5332-73-0

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Product Details of [ 5332-73-0 ]

CAS No. :5332-73-0
Formula : C4H11NO
M.W : 89.14
SMILES Code : NCCCOC
MDL No. :MFCD00014831
InChI Key :FAXDZWQIWUSWJH-UHFFFAOYSA-N
Pubchem ID :1672

Safety of [ 5332-73-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314-H226
Precautionary Statements:P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405
Class:8(3)
UN#:2734
Packing Group:

Application In Synthesis of [ 5332-73-0 ]

* 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 [ 5332-73-0 ]

[ 5332-73-0 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 475216-25-2 ]
  • [ 5332-73-0 ]
  • [ 658700-24-4 ]
YieldReaction ConditionsOperation in experiment
99% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; A solution of [4-FLUORO-3-NITRO-N-METHYLBENZAMIDE] (1.00 g, 5.05 mmoles) in 15 mL dichloromethane was prepared and added dropwise to a stirred solution of 3- methoxypropylamine (0.78 mL, 7.57 mmoles) and N, N-diisopropylethylamine (2.6 mL, 15.1 mmoles) in 10 mL dichloromethane. After stirring at room temperature overnight, TLC (EtOAc) revealed complete conversion to a lower Rf product. The mixture was diluted with ethyl acetate and washed successively with [1] M [HCI,] saturated aqueous [NAHCO3] and brine. The organic extracts were dried over [MGS04,] filtered and concentrated in vacuo to leave an orange solid residue. The crude product was dissolved in dichloromethane, adsorbed onto silica gel and then purified by flash column chromatography on silica gel. Elution with ethyl acetate provided pure fractions which were combined and concentrated to yield [4- (3-METHOXYPROPYLAMINO)-3-NITROPHENYL-N-] methylbenzamide as an orange solid product (1.34 g, [99%). IH] NMR [(CDC13)] was consistent with the desired product.
  • 2
  • [ 15441-06-2 ]
  • [ 5332-73-0 ]
  • [ 887003-99-8 ]
YieldReaction ConditionsOperation in experiment
68.4% With triethylamine; at -5 - 20℃; for 24.5 - 25.5h; In a 500ml three neck flask equipped with a stirrer, a condenser and a thermometer, 26.7g(0.3mol) gamma-methoxypropylamine, 2.5ml triethylamine are added sequentially, the temperature of the reaction system was controlled to -5-5°C and maintained. Then 23.8g (0.1mol) beta-dimethyl dithiodipropionate prepared by the front step was dropped during 0.5-1.5 hours. After dropwise addition, the ice water bath was removed. The reaction was left standing for 24 hours under the room temperature, and then the reaction was over. A golden solid was obtained. And a light yellow solid product was yielded by vacuum filtration. After dried it was recrystallized with anhydrous alcohol. 24.1g white chip crystal was obtained, and the yield is 68.4percent, the boiling point is 103.3-105.1°C.
  • 3
  • [ 207399-07-3 ]
  • [ 5332-73-0 ]
  • [ 1255954-99-4 ]
  • 4
  • [ 2106-49-2 ]
  • [ 5332-73-0 ]
  • [ 1248906-80-0 ]
YieldReaction ConditionsOperation in experiment
78% With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere; 1-Chloro-2-fluoro-3-nitrobenzene (2.85 mmol, 0.500 g) was added to an oven dried 50 mL round-bottomed flask equipped for stifling under nitrogen. Dichlormethane (10 mL) and triethylamine (3.13 mmol, 0.437 mL) were added and the resultant solution was cooled to 0 C. with an ice-bath. 3-Methoxypropan-1-amine (2.85 mmol, 0.292 mL) was then added drop-wise via syringe and the resultant solution was stirred at 0 C. for 1 hr. The ice-bath was removed and the reaction was allowed to warm to room temperature and stirred for 16 hr. The reaction solution was poured into water and extracted twice with dichloromethane (50 mL). The organic layer was collected and water was subsequently removed with anhydrous Na2SO4 and the suspension was filtered. The filtrate was collected, concentrated, and dried in-vacuo affording an orange oil, which was then purified by chromatography on slica gel (10-70% ethyl aetate/hexanes) to afford 2-chloro-N-(3-methoxypropyl)-6-nitroaniline (30A) as a yellow solid (2.23 mmol, 0.542 g, 78% yield). ESI-MS: m/z 245.3 (M+H)+.
  • 5
  • [ 5779-93-1 ]
  • [ 5332-73-0 ]
  • C13H19NO [ No CAS ]
  • 6
  • [ 1214342-44-5 ]
  • [ 5332-73-0 ]
  • 3-bromo-5-fluoro-N-(3-methoxypropyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
19.4 g With triethylamine; In dichloromethane; at 20℃; for 16h; Step 3: Preparation of 3-bromo-5-fluoro-N-(3-methoxypropyl)benzenesulfonamide To a solution of <strong>[1214342-44-5]3-bromo-5-fluoro-benzenesulfonyl chloride</strong> (23.0 g, 84.12 mmol) in DCM (250 mL) was added 3-methoxypropylamine (8.25 g, 92.53 mmol) and Et3N (25.5 g, 252.3 mmol). The mixture was stirred at rt for 16 hrs, and then partitioned between DCM (200 mL) and water (200 mL). The organic layer was separated, then washed with brine (200 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography to give 3-bromo-5-fluoro-N-(3-methoxypropyl)benzenesulfonamide (19.4 g) as a yellow oil.
  • 7
  • [ 118591-58-5 ]
  • [ 5332-73-0 ]
  • C8H19NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With potassium carbonate; In 1,4-dioxane; at 70℃; Compound 1-3 (3.5 g, 13.5 mmol) was dissolved in 1,4-dioxane (50 mL), followed by addition of methoxypropylamine 4-1 (4.81 g, 54 mmol), and potassium carbonate (5.52 g, 40 mmol) was added under stirring in batches, followed by stirring the reaction overnight under at 70° C., TLC monitoring showed that the starting material 1-3 was completely reacted. The solvent was removed under reduced pressure to obtain a concentrated residue. The concentrated residue was dispensed with dichloromethane (20 mL), an appropriate amount of silica gel was added and the sample was stirred, spin-dried under reduced pressure and directly placed on a silica gel column for column chromatographic purification, with an eluent (dichloromethane:methanol=20/1-5/1) to obtain the target product 4-2 (1.6 g, 67percent) as a pale yellow oil, LC-MS: m/z=178[M+H]+.
  • 8
  • [ 848398-41-4 ]
  • [ 5332-73-0 ]
  • C10H14ClN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 60℃; General procedure: A solution of <strong>[848398-41-4]2,4-dichloro-5,7-dihydrofuro[3,4-d]pyrimidine</strong> (4, 1.89g, 10mmol) in DMSO (10mL) was added commercially available 3,4-dimethoxyaniline (1.53g, 10mmol) and DIPEA (2.58g, 20mmol). The solution was heated to 60C and stirred overnight. Then the solution was poured into water and extracted with EtOAc, the organic layer was washed by brine, dried with anhydrous Na2SO4, and filtered and concentrated under reduced pressure. The crude product was further purified by flash chromatography on silica gel (EtOAc/hexane=1:1) to afford 8 compound 5 (2.00g, yield 65%) as an off-white solid. 1H NMR (400MHz, CDCl3) delta: 6.90-6.81 (m, 3H), 4.88 (s, 2H), 4.42 (s, 2H), 3.92 (s, 3H), 3.89 (s, 3H).
 

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