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[ CAS No. 82477-59-6 ] {[proInfo.proName]}

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Product Details of [ 82477-59-6 ]

CAS No. :82477-59-6 MDL No. :MFCD18431944
Formula : C9H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QYMODTQQSQJFJQ-UHFFFAOYSA-N
M.W : 167.21 Pubchem ID :12909334
Synonyms :

Safety of [ 82477-59-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 82477-59-6 ]

* 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 [ 82477-59-6 ]

[ 82477-59-6 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 50342-31-9 ]
  • [ 82477-59-6 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In ethanol; ethyl acetate for 1h; A.125 Example 125; N-(2,4-dimethoxy-5-methylphenyl)-N'-(5-methylisoxazol -3-yl)urea. Sodium methoxide, prepared from sodium (0.32 g, mmol) and MeOH, is added dropwise to a solution of 1-chloro-5-methoxy-3-methyl-2-nitrobenzene (2.77 g, 13.74 mmol) dissolved MeOH cooled to 0° C. The mixture is warmed to RT and then heated under reflux until reaction is complete (as judged by TLC). The reaction mixture is cooled, quenched with 1M citric acid and concentrated in vacuo. The residue is diluted in EtOAc and 1M citric acid. The aqueous layer is extracted with EtOAc. The combined organic layers are washed with brine, dried (MgSO4), filtered and concentrated to provide 2.94 g (>100% yield) of 1,5-dimethoxy-2-methyl-4-nitrobenzene sufficiently pure for further use. 1H NMR (CDCl3, 400 MHz) δ 7.85, 6.45, 3.98, 3.93, 2.16. 1,5-Dimethoxy-2-methyl-4-nitrobenzene (2.74 g, mmol) and a catalytic amount of 10% Pd/C (150 mg) are mixed in EtOH/EtOAc and shaken on a Parr hydrogenator apparatus in the presence of 40 psi H2. After 60 min, the mixture is filtered through a pad of Celite. The solvent is removed in vacuo to afford 2.35 g (100% yield) of 2,4-dimethoxy-5-methylaniline. MS for C9H13NO2 (ESI) (M+H)+ m/z 168. 2,4-Dimethoxy-5-methylaniline (1.03 g, 6.14 mmol), dissolved in 125 mL EtOAc, is added dropwise over 1 h to excess phosgene (27.7 mL, 20% solution in toluene) dissolved in EtOAc. The solution is heated under reflux for 30 min, cooled and concentrated in vacuo to provide 1.21 g (100% yield) of 1-isocyanato-2,4-dimethoxy-5-methylbenzene. MS for C10H11NO3 (ESI) (M+H)+ m/z 194. Example 125 is obtained from 1-isocyanato-2,4-dimethoxy-5-methylbenzene and 3-amino-5-methylisoxazole according to Method A, making non-critical changes. Yield 39%. HRMS (FAB) calculated for C14H17N3O4+H 292.1297, found 292.1288.
bei der Reduktion;
  • 3
  • [ 82477-57-4 ]
  • [ 82477-59-6 ]
YieldReaction ConditionsOperation in experiment
2.5 g With hydrogen; triethylamine In ethanol
YieldReaction ConditionsOperation in experiment
entspr. 2-Chlor-amin (2), H2/Pd/C;
2,4-Dimethoxy-1-nitro-5-chlormethyl-benzol, Sn, wss. HCl;
4-Methyl-resorcin-dimethylaether, 1) HNO3, Eg., 2) Sn, wss. HCl;
  • 5
  • [ 13362-33-9 ]
  • [ 82477-59-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 15.1 g / hydrogen chloride gas / 25 - 30 °C 2: 2.5 g / hydrogen, triethylamine / Engelhard 10percent palladium-charcoal / ethanol
  • 6
  • [ 75-44-5 ]
  • [ 82477-59-6 ]
  • [ 625119-51-9 ]
YieldReaction ConditionsOperation in experiment
100% In ethyl acetate; toluene for 1.5h; Heating / reflux; A.125 Example 125; N-(2,4-dimethoxy-5-methylphenyl)-N'-(5-methylisoxazol -3-yl)urea. Sodium methoxide, prepared from sodium (0.32 g, mmol) and MeOH, is added dropwise to a solution of 1-chloro-5-methoxy-3-methyl-2-nitrobenzene (2.77 g, 13.74 mmol) dissolved MeOH cooled to 0° C. The mixture is warmed to RT and then heated under reflux until reaction is complete (as judged by TLC). The reaction mixture is cooled, quenched with 1M citric acid and concentrated in vacuo. The residue is diluted in EtOAc and 1M citric acid. The aqueous layer is extracted with EtOAc. The combined organic layers are washed with brine, dried (MgSO4), filtered and concentrated to provide 2.94 g (>100% yield) of 1,5-dimethoxy-2-methyl-4-nitrobenzene sufficiently pure for further use. 1H NMR (CDCl3, 400 MHz) δ 7.85, 6.45, 3.98, 3.93, 2.16. 1,5-Dimethoxy-2-methyl-4-nitrobenzene (2.74 g, mmol) and a catalytic amount of 10% Pd/C (150 mg) are mixed in EtOH/EtOAc and shaken on a Parr hydrogenator apparatus in the presence of 40 psi H2. After 60 min, the mixture is filtered through a pad of Celite. The solvent is removed in vacuo to afford 2.35 g (100% yield) of 2,4-dimethoxy-5-methylaniline. MS for C9H13NO2 (ESI) (M+H)+ m/z 168. 2,4-Dimethoxy-5-methylaniline (1.03 g, 6.14 mmol), dissolved in 125 mL EtOAc, is added dropwise over 1 h to excess phosgene (27.7 mL, 20% solution in toluene) dissolved in EtOAc. The solution is heated under reflux for 30 min, cooled and concentrated in vacuo to provide 1.21 g (100% yield) of 1-isocyanato-2,4-dimethoxy-5-methylbenzene. MS for C10H11NO3 (ESI) (M+H)+ m/z 194. Example 125 is obtained from 1-isocyanato-2,4-dimethoxy-5-methylbenzene and 3-amino-5-methylisoxazole according to Method A, making non-critical changes. Yield 39%. HRMS (FAB) calculated for C14H17N3O4+H 292.1297, found 292.1288.
98% In ethyl acetate; toluene Heating / reflux; B.200 METHOD B; Example 200; N-(2,4-dimethoxy-5-methylphenyl)-N'-[3-(trifluoromethyl)isoxazol-5-yl]urea. 2,4-Dimethoxy-5-methylaniline (0.22 g, 1.3 mmol) is added dropwise as a solution in EtOAc (25 mL) to a phosgene solution (5.6 mL, 20% solution in toluene) in EtOAc (50 mL). After complete addition, the reaction is heated under reflux for 0.5 h. The reaction is cooled to RT and the solvent is removed under reduced pressure to give 1-isocyanato-2,4-dimethoxy-5-methylbenzene as a light brown solid (0.25 g, 98% yield). Sodium hydride (44 mg, 1.1 mmol, 60% oil disp.) is added to 3-(trifluoromethyl)isoxazole-5-amine (0.17 g, 1.1 mmol) in THF (5 mL) at 0° C. After 0.5 h, a THF solution (5 mL) of 1-isocyanato-2,4-dimethoxy-5-methylbenzene (0.19 g, 1.0 mmol) is added dropwise. The reaction is warmed to RT. After 2 h, concentrated HCl is added until the pH<5 and the solvent is removed. The crude material is purified by chromatography (Biotage 40S, 1:1 EtOAc:hexanes). The solid is recrystallized (EtOAc/hexanes) to give Example 200 as an off-white solid (135 mg, 39% yield). HRMS calcd for C14H14F3N3O4+H 346.1014 found 346.1016.
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