3-(2-O×o-pyrrolidin-1-yl)benzenesulfonyl chloride synthesis

3synthesis methods

Product Name:3-(2-O×o-pyrrolidin-1-yl)benzenesulfonyl chloride
CAS Number:344312-54-5
Molecular formula:C10H10ClNO3S
Molecular Weight:259.71

31992-43-5 Synthesis

31992-43-5
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3-(2-O×o-pyrrolidin-1-yl)benzenesulfonyl chloride

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Yield:344312-54-5 22%

Reaction Conditions:

Stage #1: 1-(3-aminophenyl)pyrrolidin-2-onewith hydrogenchloride;acetic acid;sodium nitrite in water;acetonitrile at 0; for 1 h;
Stage #2: with sulfur dioxide in water;acetonitrile at 0; for 2 h;
Stage #3: with sulfur dioxide;copper dichloride in water;acetonitrile at 0 - 20; for 17 h;

Steps:

5.3

Hydrochloric acid (11 mL) was added to a solution of l-(3-aminophenyl)pyrrolidin-2-one (35.2 mmol) in acetic acid (21 mL) and acetonitrile (250 mL)at 0 °C. A solution of sodium nitrite (42.0 mmol) in water (3 mL) was subsequently added and the mixture was maintained for 60 min at 0 °C. Sulfur dioxide gas was bubbled through the solution for 2 h while the temperature was maintained at 0 oC. A solution of copper(II) chloride dihydrate (38.8 mmol) in water (5 mL) was added dropwise and sulfur dioxide gas was bubbled through the solution for an additional 60 min. The reaction mixture was allowed to warm to rt and was maintained for 16 h. The precipitated solids were collected by filtration, washed with ice water (3 x 10 mL), and dried to provide 3-(2-oxopyrrolidin-1-yl) benzene- 1-sulfonyl chloride in 22% yield as a brown solid. Data: ¹HNMR (400MHz, CDCl₃) δ 8.27 (d, 1H), 8.14 (s, 1H), 7.80 (d, 1H), 7.61 (t, 1H), 3.94 (t, 2Ht), 2.68 (t, 2H), 2.24 (t, 2H). LC/MS (ES) m/z 329 [M+BnNH-H]-.

References:

WO2009/23844,2009,A2 Location in patent:Page/Page column 92-93

99-09-2 Synthesis

99-09-2
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References

61372-79-0 Synthesis

61372-79-0
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$28.60/50MG

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References