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[ CAS No. 53297-70-4 ]

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Chemical Structure| 53297-70-4
Chemical Structure| 53297-70-4
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CAS No. :53297-70-4 MDL No. :MFCD00466840
Formula : C7H10N2O2S Boiling Point : 409.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :186.23 g/mol Pubchem ID :143037
Synonyms :

Safety of [ 53297-70-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53297-70-4 ]

  • Upstream synthesis route of [ 53297-70-4 ]
  • Downstream synthetic route of [ 53297-70-4 ]

[ 53297-70-4 ] Synthesis Path-Upstream   1~3

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YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride In ethanol; water at 80℃; A mixture of N-(2-methyl-4-sulfamoylphenyl)acetamide (5.1 g, 22.3 mmol), HCl (2 N, 76.5 ml) and EtOH (100 ml) was refluxed overnight. Then the mixture was neutralized with Na2CO3 (aq) to pH = 8. The mixture was extracted with EA (80 mL x 4), dried over Na2SO4, and concentrated to obtain 4-amino-3-methylbenzenesulfonamide as a pale solid (4.9 g, yield 100percent).
100% With hydrogenchloride; water In ethanolReflux Compound 27-6 (0455) A mixture of 27-5 (5.1 g, 22.3 mmol), HCl (2 N, 76.5 ml) and EtOH (100 ml) was refluxed overnight. Then the mixture was neutralized with Na2CO3(aq) to PH=8. The mixture was extracted with EA (80 ml×4), dried over Na2SO4, and concentrated to give 27-6 as a pale solid (4.9 g, yield 100percent).
93%
Stage #1: With hydrogenchloride In ethanol; waterHeating / reflux
Stage #2: With sodium hydrogencarbonate In ethanol; water at 20℃;
A round-bottom flask was equipped with a stir bar, a reflux condenser and nitrogen on demand. Into the flask were placed sulfonamide 465 (8.4 g, 36.80 mmol), ethyl alcohol (200 mL) and 2N hydrochloric acid (128 mL). The resulting mixture was allowed to heat to reflux overnight, after which time it was allowed to cool to RT and was neutralized with saturated, aqueous sodium bicarbonate. It was then poured into a separatory funnel containing water and ethyl acetate, the organic layer was collected, washed with water, brine, dried over MgSO4, filtered and the solvents were removed under reduced pressure to afford a tan solid (6.35 g, 93percent), which was used without further purification. 1H NMR (DMSO-d6, 400 MHz) δ 2.06 (s, 3H), 5.54 (s, 2H), 6.58 (d, J= 12 Hz, 1H), 6.82 (s, 2H), 7.30 (d, J= 12 Hz, 1H), 7.33 (s, 1H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 6, p. 2338 - 2342
[2] Patent: US9138427, 2015, B2, . Location in patent: Page/Page column 304
[3] Patent: EP1208091, 2006, B1, . Location in patent: Page/Page column 8; 21
[4] Collection of Czechoslovak Chemical Communications, 1948, vol. 13, p. 161,165,169
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 5, p. 1175 - 1182
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Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 5, p. 1175 - 1182
[2] Patent: US9138427, 2015, B2,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 6, p. 2338 - 2342
[2] Patent: US9138427, 2015, B2,
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