Chlorosulfonic acid → HCID 55280640, compound

HRID 641903Notes

Reaction equation

HRID 641903 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].[Cl:12][S:13](O)(=[O:15])=[O:14]>>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([S:13]([Cl:12])(=[O:15])=[O:14])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 524514HCID 524514, compound

Product 1

HCID 55280640HCID 55280640, compoundYield 6%

Conditions

Temperature
50 °C

Procedure

1-ethylindoline (15 g, 102.04 mmol) was added at 0° C. to ClSO3H (60 g). The resulting solution was stirred at 50° C. overnight, then the reaction was quenched by adding 300 g iced water. The resulting solution was extracted with dichloromethane (3×600 mL) and the organic layers were combined, dried (MgSO4) and concentrated. The residue was then purified by column chromatography using a 1:100 ethyl acetate/petroleum ether solvent system to give 1.5 g (6%) of 1-ethylindoline-5-sulfonyl chloride as a yellow solid. 1H NMR (CDCl3) δ 7.28 (d, 1H), 7.18 (d, 1H), 7.11 (s, 1H), 3.39 (q, 2H), 3.52 (t, 2H), 3.06 (t, 2H), 1.23 (t, 3H).

Workup

  1. customthe reaction was quenched
  2. additionby adding 300 g iced water
  3. extractionThe resulting solution was extracted with dichloromethane (3×600 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-beb175ea3e0b4dc98a1f82452bad4aa8
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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