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[ CAS No. 1483-28-9 ] {[proInfo.proName]}

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Chemical Structure| 1483-28-9
Chemical Structure| 1483-28-9
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Product Details of [ 1483-28-9 ]

CAS No. :1483-28-9 MDL No. :MFCD00024872
Formula : C8H9ClO4S Boiling Point : -
Linear Structure Formula :- InChI Key :SHELADVIRCCTFN-UHFFFAOYSA-N
M.W :236.67 Pubchem ID :137025
Synonyms :

Safety of [ 1483-28-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1483-28-9 ]

* 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 [ 1483-28-9 ]

[ 1483-28-9 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 1483-28-9 ]
  • [ 19116-91-7 ]
YieldReaction ConditionsOperation in experiment
78% With hydrazine hydrate In tetrahydrofuran at 0 - 20℃; 8 4.1.2.8
2,5-Dimethoxybenzenesulfonohydrazide (5p) General procedure: To solution of 1 mmol of arylsulfonyl chloride 4i-w in 10 ml of THF, 1.1 mmol of hydrazine-hydrate in 10 ml THF were added drop wise at 0-5 8C with stirring. After stirring 1-2 h at rt 20 ml of water were added, the precipitate was filtered, dried and crystallized from benzene or hexane. HPLC analysis revealed single peaks for all tested compounds. Yield 78%, m.p. 98-100 °C. 1H NMR (DMSO-d6): δ 3.82 (s, 3H, CH3O), 3.90 (s, 3H, CH3O), 7.22 (m, 2H, HAr), 7.31 (d, 1H, JHH = 2.6 Hz, HAr), 7.74 (s, 1H, NH). EI-MS (m/z): 233 [M+1]+. Anal. calcd. for C8H12N2O4S: C, 41.37; H, 5.21; N, 12.06; O, 27.55; S, 13.81; found: C, 41.52; H, 5.38; N, 12.29.
With hydrazine hydrate
With hydrazine hydrate In water; toluene for 15h; Ambient temperature;
  • 2
  • [ 1483-28-9 ]
  • [ 19116-90-6 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide
With ammonium hydroxide; ethyl acetate at 20℃; for 16h;
With ammonia In tetrahydrofuran 6.A Step A Step A 2,5-Dimethoxyphenylsulfonamide To a stirred solution of 15.0 g (0.063 mole) of 2,5-dimethoxybenzenesulfonyl chloride in 150 mL of tetrahydrofuran was added dropwise 80 mL of ammonia (28% aqueous solution). After complete addition the mixture was allowed to stir for 1.75 hours at room temperature. Upon standing the mixture separated into two phases. The organic phase was removed from the aqueous phase and was evaporated under reduced pressure to leave a solid residue. This residue was recrystallized from hot water (125 mL) and ethanol (40 mL) to yield 13.1 g of 2,5-dimethoxyphenylsulfonamide (mp 146.5-148.5).
With ammonia In tetrahydrofuran 14.A Step A Step A 2,5-Dimethoxyphenylsulfonamide To a stirred solution of 15.0 g (0.063 mole) of 2,5-dimethoxybenzenesulfonyl chloride in 150 mL of tetrahydrofuran was added dropwise 80 mL of ammonia (28% aqueous solution). After complete addition the mixture was allowed to stir for 1.75 hours at room temperature. Upon standing the mixture separated into two phases. The organic phase was removed from the aqueous phase and was evaporated under reduced pressure to leave a solid residue. This residue was recrystallized from hot water (125 mL) and ethanol (40 mL) to yield 13.1 g of 2,5-dimethoxyphenylsulfonamide (mp 146.5-148.5).

  • 4
  • [ 1483-28-9 ]
  • [ 33084-49-0 ]
  • 2,5-dimethoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% EXAMPLE 201 2,5-Dimethoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 2,5-Dimethoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2,5-dimethoxybenzenesulfonyl chloride according to the procedures described in Example 200. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 118-120, yield 58%.
58% EXAMPLE 48 2,5-Dimethoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 2,5-Dimethoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2,5-dimethoxybenzenesulfonyl chloride according to the procedures described in Example 5. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 118-120 C. yield 58%.
  • 5
  • [ 1483-28-9 ]
  • [ 144-55-8 ]
  • [ 6153-39-5 ]
  • 3-(2,5-dimethoxyphenylsulfonyloxy)-5-methylphenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.29 g (54%) a 3-(2,5-Dimethoxyphenylsulfonyloxy)-5-methylphenol To a solution of 1.00 g (8.05 mmol) of <strong>[6153-39-5]orcinol monohydrate</strong> and 1.75 g (7.38 mmol) of 2,5-dimethoxybenzenesulfonyl chloride in 20 mL of diethyf ether was added 20 mL of saturated aqueous NaHCO3 and the biphasic mixture stirred vigorously at ambient temperature for 3 days. The layers were separated and the aqueous layer extracted with 2*30 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried (Na2 SO4) and concentrated to give an amber-colored solid. Recrystallization from ethyl acetate-hexane afforded 1.29 g (54%) of the title compound as a cream-colored powder: 1 H-NMR (300 MHz; CDCl3) delta 7.34 (d, 1 H, J=3.1 Hz), 7.15 (dd, 1 H, J=9.1, 3.1 Hz), 7.02 (d, 1 H, J=9.1 Hz), 6.53 (m, 2 H), 6.42 (t, 1H, J=2.2 Hz), 5.08 (br s, 1 H),3.95 (s,3 H), 3.76 (s, 3 H), and 2.23 (s, 3 H).
  • 6
  • [ 504-15-4 ]
  • [ 1483-28-9 ]
  • 3-(2,5-dimethoxyphenylsulfonyloxy)-5-methylphenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With sodium hydrogencarbonate In diethyl ether; water at 20℃; for 72h; 16.a a) a) 3-(2,5-Dimethoxyphenylsulfonyloxy)-5-methylphenol To a solution of 1.00 g (8.05 mmol) of orcinol monohydrate and 1.75 g (7.38 mmol) of 2,5-dimethoxybenzenesulfonyl chloride in 20 mL of diethyl ether was added 20 mL of saturated aqueous NaHCO3 and the biphasic mixture stirred vigorously at ambient temperature for 3 days. The layers were separated and the aqueous layer extracted with 2 x 30 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried (Na2SO4) and concentrated to give an amber-colored solid. Recrystallization from ethyl acetate-hexane afforded 1.29 g (54%) of the title compound as a cream-colored powder: 1H-NMR (300 MHz; CDCl3) δ 7.34 (d, 1 H, J = 3.1 Hz), 7.15 (dd, 1 H, J = 9.1, 3.1 Hz), 7.02 (d, 1 H, J = 9.1 Hz), 6.53 (m, 2 H), 6.42 (t, 1 H, J = 2.2 Hz), 5.08 (br s, 1 H), 3.95 (s, 3 H), 3.76 (s, 3 H), and 2.23 (s, 3 H).
  • 7
  • concentrated H2 SO4 [ No CAS ]
  • [ 1483-28-9 ]
  • [ 1483-27-8 ]
YieldReaction ConditionsOperation in experiment
With zinc; In tetrahydrofuran; water; a. 16 g of 2,5-dimethoxybenzene-sulphonyl chloride are dissolved in 100 ml of THF, while stirring, and a mixture of 20 ml of concentrated H2 SO4 and 60 ml of water is then added, followed by 25 g of zinc dust, added in portions at 50-55 and stirring is continued overnight at 20. The THF is then stripped off and the mixture is worked up with water and methylene chloride to give 2,5-dimethoxythiophenol, b.p. 106-108/0.3 mm.
  • 8
  • [ 3334-05-2 ]
  • [ 1483-28-9 ]
  • (R)-3-[(2,5-dimethoxybenzenesulfonyl)oxy]tetrahydrothiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap In dichloromethane at 5 - 20℃; 11 4.2.2 (R)-3-[(Methanesulfonyl)oxy]tetrahydrothiophene 4 (R)-4 General procedure: 4.2.2 (R)-3-[(Methanesulfonyl)oxy]tetrahydrothiophene 4 (R)-4 Compound (R)-1 (3.0 g, 28.8 mmol) was dissolved in CH2Cl2 (30 mL) and cooled to 5 °C. To this solution were added DMAP (5.28 g, 43.2 mmol) and methanesulfonyl chloride (3.96 g, 34.6 mmol) at 5 °C, and the mixture was stirred overnight at room temperature. After monitoring that the reaction was complete by TLC (hexane/EtOAc 1:1), 1 M HCl (15 mL) was added. The two layers were separated, and the aqueous layer was extracted with CH2Cl2 (2 * 10 mL). All organic layers were washed with brine, and dried (Na2SO4). The solvent was evaporated in vacuum to provide crude (R)-4. The crude was purified by silica gel chromatography (hexane/EtOAc 2:1-1:1, stepwise) to yield (R)-4 (4.59 g, 87%) as a pale yellow oil
  • 9
  • [ 116797-02-5 ]
  • [ 1483-28-9 ]
  • 1'-((2,5-dimethoxyphenyl)sulfonyl)-4-methyl-1,4'-bipiperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;
  • 10
  • [ 36216-80-5 ]
  • [ 1483-28-9 ]
  • N-(benzo[d]isoxazol-3-yl)-2,5-dimethoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 20℃; for 16h; Method BA A mixture of <strong>[36216-80-5]benzo[d]isoxazol-3-amine</strong> and a sulfonyl chloride in pyridine (1 ml.) was stirred at room temperature for 16 hours. The reaction was concentrated and diluted with 5% aqueous HCI (1 ml.) and sonicated for a minimum of 30 minutes. The resulting precipitate was collected by filtration or DCM extraction (2x1 ml.) and purified using silica gel column chromatography (EtOAc/petroleum benzine 40-60 C gradient) or preparative mass-directed HPLC to give the desired product. See Table B for reaction components and amounts used as well as purification conditions.
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