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Chemical Structure| 80789-74-8 Chemical Structure| 80789-74-8

Structure of 80789-74-8

Chemical Structure| 80789-74-8

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Product Details of [ 80789-74-8 ]

CAS No. :80789-74-8
Formula : C8H4NNaO5S
M.W : 249.18
SMILES Code : O=S(C1=CC2=C(NC(C2=O)=O)C=C1)([O-])=O.[Na+]
MDL No. :MFCD00055993

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Application In Synthesis of [ 80789-74-8 ]

* 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 [ 80789-74-8 ]

[ 80789-74-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 80789-74-8 ]
  • [ 132898-96-5 ]
YieldReaction ConditionsOperation in experiment
83% With trichlorophosphate; In sulfolane; at 60℃; for 3h; (16) Phosphorus oxychloride (13.2 mL, 141.6 mmol) was added to a solution of 5-isatinsulfonic acid (5), sodium salt hydrate (8.0 g, 30.0 mmol) in tetramethylene sulfone (40 mL). The mixture was heated to 60 C. for 3 h, then cooled to 0 C. The reaction mixture was poured into 150 g of ice. The solid was filtered out and washed with cold water, then the solid was dissolved in ethyl acetate (100 mL), washed with water (50 mL*2) and saturated NaCl (50 mL), and dried over Na2SO4. The ethyl acetate was evaporated in reduced pressure to afford 6.12 g (83%) of 6 as a pale yellow solid, mp 188.2-190.1 C. 1H NMR (300 MHz, DMSO) delta 11.1 (s, 1H), 7.82 (dd, J=8.4 Hz, J=1.8 Hz, 1H), 7.60 (s, 1H), 6.89 (d, J=8.1 Hz, 1H).
82% With trichlorophosphate; at 60℃; for 3h; A suspension of sodium 2,3-dioxoindoline-5-sulfonate dihydrate (5.0 g, 17.53 mmol) and POCl3 (8.17 ml, 88 mmol) in sulfolane (25 ml, 264 mmol) was heated at 60 C. for 3 hours. The solution was cooled to 0 C. and water (60 ml) was added drop wise; the green precipitate was filtered and washed with a small amount of water. The solid was dissolved in ethyl acetate and washed three times with water; the organic phase was then dried over sodium sulfate and evaporated to give a crude solid that was purified by crystallization from hexane/ethyl acetate 1:1 to give 2,3-dioxoindoline-5-sulfonyl chloride (3.52 g, 14.33 mmol, 82% yield).
82% With trichlorophosphate; In sulfolane; at 60℃; for 3h; Example 27 (S)-3,5-Dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy) phenyl)-2-(2-(5-(N,N-dimethylsulfamoyl)-2,3-dioxoindolin-1 -yl)acetoxy)- ethyl)pyridine 1 -oxide (compound 151 ) Scheme 27 Step 1 : Preparation of 2,3-dioxoindoline-5-sulfonyl chloride (147) A suspension of sodium 2,3-dioxoindoline-5-sulfonate dihydrate (5.0 g, 17.53 mmol) and POCI3 (8.17 ml, 88 mmol) in sulfolane (25 ml, 264 mmol) was heated at 60C for 3 hours. The solution was cooled to 0C and water (60 ml) was added drop wise; the green precipitate was filtered and washed with a small amount of water. The solid was dissolved in ethyl acetate and washed three times with water; the organic phase was then dried over sodium sulfate and evaporated to give a crude solid that was purified by crystallization from hexane/ethyl acetate 1 : 1 to give 2,3-dioxoindoline-5-sulfonyl chloride (3.52 g, 14.33 mmol, 82% yield).
68% With trichlorophosphate; In sulfolane; at 60℃; for 3h; Phosphorus oxychloride (27.17 g, 177.2 mmol) was added to a mixture of 5- isatinsulfonic acid sodium salt dihydrate (10.1 g, 35.5 mmol) in of tetramethylene sulfone (50 ml). The resulting mixture was stirred at 60 0C for 3 h. After cooling to 0 0C, water (120 ml) was added. The green precipitate was filtered, dissolved in ethyl acetate (200 ml) and washed with water (150 ml). The organic extracts were collected, dried over Na2SO4, filtered and the solvent removed under reduced pressure to provide a green solid. The pure compound rpm 121 was obtained after recrystallization from ethyl acetate/hexane 1 : 1 as yellow solid (5.9 g, 21.1 mmol, 68 %). 1H NMR (400 MHz, CDC13:CD3CN 1 :1) delta 7.22 (IH, d, J 8.4 Hz), 8.16 (IH, d, J2.0 Hz), 8.23 (IH, dd, / 8.4, 2.0 Hz), 9.47 (IH, s), mp 200- 202 0C.
66% With trichlorophosphate; In sulfolane; at 60℃; for 3h; Step 1: 2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride A mixture of isatinsulfonic acid sodium salt hydrate (10.00 g, 39.7 mmol) and phosphorous oxychloride (18.5 mL, 199 mmol, 5 eq) in tetramethylene sulfone (50 mL) was heated at 60 C. for 3 hours under a dry N2 atmosphere. The reaction was cooled in an ice bath to 0 C. and water was cautiously added drop-wise, keeping the internal temperature below 6 C. The resulting green solid was collected by filtration and was washed well with water. The solid was dissolved in ethyl acetate (200 mL) and washed again with water (3*50 mL), dried over magnesium sulfate, filtered and concentrated to give the crude product in 85% yield. The solid was recrystallized from ethyl acetate: hexanes with hot filtration to give the title compound (5.81 g, 66% yield). NMR (400 MHz, DMSO-d6): consistent.

  • 2
  • [ 615-06-5 ]
  • [ 80789-74-8 ]
  • [ 854948-62-2 ]
 

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