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[ CAS No. 194032-34-3 ] {[proInfo.proName]}

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Chemical Structure| 194032-34-3
Chemical Structure| 194032-34-3
Structure of 194032-34-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 194032-34-3 ]

CAS No. :194032-34-3 MDL No. :MFCD27991791
Formula : C9H5Cl2NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 262.11 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 194032-34-3 ]

* 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 [ 194032-34-3 ]

[ 194032-34-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1532-91-8 ]
  • [ 194032-34-3 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 16 1-[(4-Chloro-5-isoquinolinyl)sulfonyl]-hexahydro-1H-1,4-diazepine dihydrochloride Using 2.08 g of <strong>[1532-91-8]4-chloroisoquinoline</strong> (synthesised in accordance with J. Org. Chem., 1961, 26, 468), 4-chloro-5-chlorosulfonylisoquinoline was synthesised as in Reference Example 1.
  • 2
  • [ 651310-21-3 ]
  • [ 194032-34-3 ]
YieldReaction ConditionsOperation in experiment
46% Stage #1: 4-chloroisoquinolin-5-amine With hydrogenchloride; sodium nitrite In water at -5℃; for 1h; Stage #2: With sulfur dioxide; acetic acid; copper(l) chloride In water at 20℃; 16.3 To a solution of 4-chloroisoquinolin-5-amine (1.57 g, 8.82 mmol) in 14 mL concentrated hydrochloric acid was added a solution of NaNO2 (620 mg, 8.82 mmol) in 2 mL water at -5° C., and the resulting mixture was allowed to stir for 1 h at this temperature, and then was transferred to a solution of 30 mL acetic acid with CuCl (224 mg, 2.20 mmol, in 2 mL water) saturated by SO2 in one portion. The reaction was stirred at room temperature until no more bubble formed. To the reaction mixture was added 100 mL ice water, and the pH was adjusted to 8 using saturated aq. NaHCO3. The mixture was then extracted with dichloromethane (100 mL*2), the combined organic layers were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated to give 4-chloroisoquinoline-5-sulfonyl chloride 16d (1.07 g, yellow solid, yield: 46%). MS-ESI calc'd. [M+H]+ 262, found 262.
Stage #1: 4-chloroisoquinolin-5-amine With hydrogenchloride; sodium nitrite In water at -5℃; for 1h; Inert atmosphere; Stage #2: With sulfur dioxide; acetic acid; copper(l) chloride In water for 2.5h; 27 Preparation of Solution 1: To a mixture of 4-chloroisoquinolin-5-amine (1.5 g, 8.40 mmol, 1 eq) in conc. HCl (15 mL) was added NaNO2 (579.45 mg, 8.40 mmol, 1 eq) in one portion at -5° C. under N2. The mixture was stirred at -5° C. for 1 hr. Preparation of Solution 2: SO2 was bubbled into a solution of CuCl (207.85 mg, 2.10 mmol, 0.25 eq) in HOAc (15 mL) and H2O (3 mL) at 0° C. for 30 minutes. Compound 27-4: To solution 1 solution 2 was added slowly. The mixture was stirred at 15° C. for 2 hr. The reaction mixture was concentrated under reduced pressure to remove solvent. The residue was diluted with H2O (500 mL) and extracted with DCM (300 mL*3). The combined organic layers were washed with brine (500 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue that was used with no further purification. Compound 27-4, 4-chloroisoquinoline-5-sulfonylchloride (1.5 g, crude), was obtained as a yellow solid.
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