Chlorosulfonic acid → 173669-61-9

HRID 641898Notes

Reaction equation

HRID 641898 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1>>[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:14]=2)[CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 558301-Methyl-2,3-dihydro-1H-indole

Product 1

HCID 55279539173669-61-9Yield 7%

Conditions

Temperature
0 °C

Procedure

ClSO3H (400 g, 3.45 mol) was cooled to 0° C. and 1-methylindoline (35 g, 263.16 mmol) was added dropwise with stirring, maintaining the temperature at 0° C. The resulting solution was then warmed to room temperature and stirred for 20 hours. The reaction mixture was added carefully then dropwise to 3 L of iced water and the resulting solution was extracted using dichloromethane (3×400 mL). The organic layers were combined, dried (Na2SO4) and concentrated. The resulting residue was purified by column chromatography using a 1:30 ethyl acetate/petroleum ether solvent system. The collected fractions were combined and concentrated to give 4.2 g (7%) of 1-methylindoline-6-sulfonyl chloride as a brown solid. 1H NMR (CDCl3) δ 7.34 (d, 1H), 7.20 (d, 1H), 6.95 (s, 1H), 3.52 (t, 2H), 3.08 (t, 2H), 2.86 (s, 3H).

Workup

  1. temperatureThe resulting solution was then warmed to room temperature
  2. stirringstirred for 20 hours
  3. additionThe reaction mixture was added carefully
  4. extractiondropwise to 3 L of iced water and the resulting solution was extracted
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-69469cce94d2425b90a1a6f58e3116dc
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

Loading…