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[ CAS No. 42247-91-6 ] {[proInfo.proName]}

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Chemical Structure| 42247-91-6
Chemical Structure| 42247-91-6
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Product Details of [ 42247-91-6 ]

CAS No. :42247-91-6 MDL No. :MFCD11185144
Formula : C8H10N2O5S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 246.24 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 42247-91-6 ]

* 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 [ 42247-91-6 ]

[ 42247-91-6 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 15020-57-2 ]
  • [ 42247-91-6 ]
YieldReaction ConditionsOperation in experiment
55% With sulfuric acid; nitric acid at -20℃;
7.85 grams (63.8%) With nitric acid In sulfuric acid 11 Preparation of N,N-Dimethyl-2-nitro-1-phenol-4-sulfonamide EXAMPLE 11 Preparation of N,N-Dimethyl-2-nitro-1-phenol-4-sulfonamide Nitric acid (d. 1.42, 3.5 ml., 0.075 mole) dissolved in sulfuric acid is added dropwise with cooling to a solution of N,N-dimethyl-1-phenol-4-sulfonamide (10.0 grams, 0.05 mole), dissolved in 12 ml. sulfuric acid and cooled to 0°C. After all of the nitric acid has been added, the entire reaction is carefully poured onto water-ice, and the yellow solid which results is recrystallized from 95% ethanol to give 7.85 grams (63.8%) product, melting point 116°C. to 118°C. Analysis Calculated for C8 H10 N2 O5 S: C, 39.02; H, 4.09; N, 11.38; S, 13.02. Found: C, 39.32; H, 4.07; N, 11.11; S, 13.22.
  • 2
  • [ 42247-91-6 ]
  • [ 24962-75-2 ]
YieldReaction ConditionsOperation in experiment
68% With hydrogen In ethanol
YieldReaction ConditionsOperation in experiment
p-HO-C6H4-SO2-NMe2, HNO3;
HNO3, H2SO4, p-HO-C6H4-SO2N(CH3)2;
  • 4
  • [ 42247-91-6 ]
  • [ 100245-58-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 68 percent / H2 / 5percent Pd/C / ethanol 2: pyridine / CH2Cl2 / 1 h / 20 °C 3: 92 percent / CF3COOH / 0.5 h / Heating
  • 5
  • [ 42247-91-6 ]
  • [ 100245-27-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 68 percent / H2 / 5percent Pd/C / ethanol 2: pyridine / CH2Cl2 / 1 h / 20 °C
  • 6
  • [ 42247-91-6 ]
  • [ 61712-36-5 ]
YieldReaction ConditionsOperation in experiment
With iron(III) chloride; bromine; acetic acid In water at 20℃; 67.2 Step 2. 3-bromo-4-hydroxy-N,N-dimethyl-5-nitrobenzenesulfonamide Step 2. 3-bromo-4-hydroxy-N,N-dimethyl-5-nitrobenzenesulfonamide Bromine (10 L, 0.2 mmol) was added to a solution of 4-hydroxy-N,N-dimethyl-3- nitrobenzenesulfonamide (50 mg, 0.2 mmol) in acetic acid (2 mL) and ferric chloride (7 mg, 0.04 mmol) in water (0.5 mL) at room temperature. The reaction was stirred overnight at room temperature then partitioned between saturated NaHC03 and ethyl acetate. The combined organic layers were washed with brine, dried over MgS04, filtered, and concentrated to afford crude 3-bromo-4-hydroxy-N,N-dimethyl-5-nitrobenzenesulfonamide (60 mg, 80%) as a glass. LCMS calculated for CsHioBr^OsS (M+H)+: m/z = 325.1, 327.1; found = 324.9, 326.9.
3.92 grams (60.4%) With sodium hydroxide; bromine In chloroform; water 12 Preparation of 2-Bromo-N,N-dimethyl-6-nitro-1-phenol-4-sulfonamide EXAMPLE 12 Preparation of 2-Bromo-N,N-dimethyl-6-nitro-1-phenol-4-sulfonamide Bromine (4.2 grams, 0.026 mole) is dissolved in 20 ml. chloroform and added slowly to a well-stirred solution of N,N-dimethyl-2-nitro-1-phenol-4-sulfonamide (5.0 grams, 0.020 mole) in 22 ml. N sodium hydroxide (0.022 mole) and 50 ml. of water. The red-brown solid which formed is removed and dissolved in ether which is washed with water, dried over MgSO4, and evaporated in vacuo. The resulting product is recrystallized from 95% ethanol to give 3.92 grams (60.4%) product, melting point 148°C. to 149°C. Analysis Calculated for C8 H9 BrN2 O5 S: C, 29.55; H, 2.79; Br, 24.58; N, 8.62. Found: C, 29.70; H, 2.78; Br, 24.42; N, 8.68.
  • 7
  • [ 42247-91-6 ]
  • 3-amino-5-bromo-4-hydroxy-N,N-dimethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bromine; iron(III) chloride; acetic acid / water / 20 °C 2: hydrogen / ethanol / 2 h / 1551.49 Torr / Inert atmosphere
  • 8
  • [ 147682-51-7 ]
  • [ 124-40-3 ]
  • [ 42247-91-6 ]
YieldReaction ConditionsOperation in experiment
With dmap In tetrahydrofuran at 20℃; 67 Step 1. 4-hydroxy-N,N-dimethyl-3-nitrobenzenesulfonamide Step 1. 4-hydroxy-N,N-dimethyl-3-nitrobenzenesulfonamide 2.0 M Dimethylamine in THF (0.2 mL, 0.4 mmol) was added to a mixture of 4- hydroxy-3-nitrobenzenesulfonyl chloride (100 mg, 0.4 mmol) (Matrix cat 084425) and 4- N,N-dimethylaminopyridine (50 mg, 0.4 mmol) in tetrahydrofuran (5 mL) at room temperature. The reaction mixture was stirred overnight then partitioned between ethyl acetate and 1 N HC1. The combined organic layers were washed with brine, dried over MgS04, filtered, and concentrated to afford crude 4-hydroxy-N,N-dimethyl-3- nitrobenzenesulfonamide as a solid (90 mg, 90%). LCMS calculated for C8H11N2O5S (M+H)+: m/z = 247.1; found = 247.0.
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