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

HRID 2211940Notes

Reaction equation

HRID 2211940 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].S(Cl)(Cl)=O.[Cl:20][S:21](O)(=[O:23])=[O:22]>>[F:15][C:2]([F:1])([F:14])[C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([S:21]([Cl:20])(=[O:23])=[O:22])=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=[O:4]

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

A solution of the 1-(trifluoroacetyl)indoline (2-1, 21.5 g), neat in thionyl chloride (65.59 mL, 899.24 mmol), was cooled to 0° C. and treated with chlorosulfonic acid (13.28 mL, 199.83 mmol). The solution was stirred for 50 minutes, then poured directly into a beaker of ice (3 L). The precipitate was filtered and vacuum dried to afford 1-(trifluoroacetyl)indoline-5-sulfonyl chloride (2-2) 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. filtrationThe precipitate was filtered
  2. customvacuum dried

Sources & evidence

ORD record
ord-2952208659854d8e895710417fbc74f9
Source dataset
uspto-grants-2006_09
Patent number
US07101884B2

Reaction notes

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