Chlorosulfonic acid → 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-sulfonyl chloride

HRID 456638Notes

Reaction equation

HRID 456638 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[C:12]([C:13]([C:15]2[NH:16][CH:17]=[CH:18][CH:19]=2)=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=1>>[Cl:6][C:7]1[C:12]([C:13]([C:15]2[NH:16][CH:17]=[C:18]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:19]=2)=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 13160528(2-Chloropyridin-3-yl)(1H-pyrrol-2-yl)methanone

Product 1

HCID 184368905-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-sulfonyl chlorideYield 95%

Conditions

Temperature
0 °C

Procedure

Chlorosulfonic acid (6.6 mL, 100 mL) was added dropwise to (2-chloro-pyridin-3-yl)-(1H-pyrrol-2-yl)-methanone (from Example 2, 2.06 g, 10 mmol) at 0° C. After stirring at 0° C. for 24 hours, the reaction was poured slowly into ice water. The precipitate was collected by vacuum filtration, washed with water and dried to give 2.9 g (95%) of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-sulfonyl chloride as a white solid.

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-83928b688d654b4f91f3984f03e42fdb
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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