Thionyl Chloride → 1-(Trifluoroacetyl)-2,3-dihydro-1H-indole-5-sulfonyl chloride

HRID 1375428Notes

Reaction equation

HRID 1375428 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]([F:20])([F:19])[C:8]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)=[O:9].S(Cl)(Cl)=O>>[F:20][C:7]([F:6])([F:19])[C:8]([N:10]1[C:18]2[C:13](=[CH:14][C:15]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)=[O:9]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 44055422,2,2-Trifluoro-1-indolinylethan-1-one

Product 1

HCID 110883061-(Trifluoroacetyl)-2,3-dihydro-1H-indole-5-sulfonyl chloride

Procedure

Chlorosulfonic acid (13.3 mL, 200 mmol, 2.00 equiv) was added to a solution of 1-(trifluoroacetyl)indoline (1-5, 21.5 g, 99.9 mmol, 1 equiv)) in thionyl chloride (65.6 mL, 899 mmol, 9.00 equiv) precooled to 0° C. The resulting mixture was stirred for 50 minutes, then poured onto ice (approx. 3 kg). The precipitate was filtered and then dried in vacuo to afford 1-(trifluoroacetyl)indoline-5-sulfonyl chloride (1-6) as an orange solid. 1H NMR (500 MHz, CDCl3) δ 8.42 (d, 1H, J=8.5 Hz), 8.00 (d, 1H, J=6.7 Hz), 7.92 (s, 1H), 4.43 (t, 2H, J=8.2 Hz), 3.41 (t, 2H, J=8.2 Hz).

Workup

  1. customprecooled to 0° C
  2. additionpoured onto ice (approx. 3 kg)
  3. filtrationThe precipitate was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-495d93d888ca417e9ed84c0f188f9c72
Source dataset
uspto-grants-2007_01
Patent number
US07169788B2

Reaction notes

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