Chlorosulfonic acid → HCID 59432940, compound

HRID 576050Notes

Reaction equation

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

Participants

Reactant 2

HCID 24638Chlorosulfonic acid

HCID 59432914HCID 59432914, compound

Product 1

HCID 59432940HCID 59432940, compoundYield 76%

Procedure

Chlorosulfonic acid (5.22 mL, 78.5 mmol) was cooled to −78° C. and 2,2,2-trichloro-1-(1,3-dihydro-2 H-isoindol-2-yl)ethanone (1.32 g, 5.00 mmol) was added thereto. The reaction mixture was warmed to room temperature and stirred for 30 min. The reaction mixture was poured into ice water and the mixture was extracted three times with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was powdered with hexane and collected by filtration to afford 2-(trichloroacetyl)-2,3-dihydro-1 H-isoindole-5-sulfonyl chloride as a pale green powder (1.38 g).

Workup

extractionthe mixture was extracted three times with ethyl acetate
concentrationThe organic layer was concentrated under reduced pressure
filtrationcollected by filtration

Sources & evidence

ORD record: ord-81de6e63212f4a42947026fc620e6115
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09035059B2

Reaction notes

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