5-(Chlorosulfonyl) Isatin synthesis

6synthesis methods

Product Name:5-(Chlorosulfonyl) Isatin
CAS Number:132898-96-5
Molecular formula:C8H4ClNO4S
Molecular Weight:245.64

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132898-96-5
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Yield:132898-96-5 83%

Reaction Conditions:

with trichlorophosphate in sulfolane at 60; for 3 h;

Steps:

1 Example 1
(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) δ 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).

References:

Washington University in St. Louis US2009/68105, 2009, A1 Location in patent:Page/Page column 9

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